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Pentamidine is an antimicrobial medication used to treat African trypanosomiasis, leishmaniasis, babesiosis, and to prevent and treat pneumocystis pneumonia (PCP) in people with poor immune function.^[1] In African trypanosomiasis it is used for early disease before central nervous system involvement, as a second line option to suramin.^[1] It is an option for both visceral leishmaniasis and cutaneous leishmaniasis.^[1] Pentamidine can be given by injection into a vein or muscle or by inhalation.^[1]

Common side effects of the injectable form include low blood sugar, pain at the site of injection, nausea, vomiting, low blood pressure, and kidney problems.^[1] Common side effects of the inhaled form include wheezing, cough, and nausea.^[1] It is unclear if doses should be changed in those with kidney or liver problems.^[1] Pentamidine is not recommended in early pregnancy but may be used in later pregnancy.^[1] Its safety during breastfeeding is unclear.^[2] Pentamidine is in the aromatic diamidine family of medications.^[3] While how the medication works is not entirely clear, it is believed to involve decreasing the making of DNA, RNA, and protein.^[1]

Pentamidine came into medical use in 1937.^[4] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.^[5] It is available as a generic medication.^[1] In regions of the world where the disease is common pentamidine is provided for free by the World Health Organization.^[6] In the United States as of 2016 the inhalation powder costs 122.84 USD and a vial for injection costs 45.31 USD a dose.^[7] Since it was found useful for PCP pneumonia the price has been increased greater than ten times.^[4]

1 Medical uses
- 1.1 Other uses
- 1.2 Special Populations
  - 1.2.1 Pregnancy
  - 1.2.2 Breastfeeding
  - 1.2.3 Children
  - 1.2.4 Elderly
2 Contraindications
3 Side effects
- 3.1 Common
- 3.2 Rare
- 3.3 Others
4 Drug interactions
5 Mechanism of action
- 5.1 Resistance
6 Pharmacokinetics
7 Chemistry
8 History
9 Trade names and dose form
10 See also
11 References

Medical uses

Treatment of PCP caused by Pneumocystis jirovecii^[8]
Prevention of PCP in adults with HIV who have one or both of the following:
- History of PCP
- CD4+ count ≤ 200mm³^[9]
Treatment of leishmaniasis^[10]
Treatment of African trypanosomiasis caused by Trypanosoma brucei gambiense^[10]
Pentamidine is classified as an orphan drug by the U.S. Food and Drug Administration^[11]

Other uses

Use as an antitumor drug has also been proposed.^[12]
Pentamidine is also identified as a potential small molecule antagonist that disrupts this interaction between S100P and RAGE receptor.^[13]

Special Populations

Pregnancy

It has not been shown to cause birth defects in animal studies when given intravenously. There are no controlled studies to show if pentamidine can harm the fetus in pregnant women. It is only recommended if the drug of choice trimethoprim-sulfamethoxazole is contraindicated.^[14]

Breastfeeding

There is no information regarding the excretion of pentamidine in breast milk, but since the adverse effects on breastfed infants are unknown currently, it is recommended by the manufacturer for the infant to not be breastfed or for the mother to stop the drug. Risks versus benefits for the mother should be considered when making this decision.^[14]

Children

Pentamidine can be used in the prevention of PCP in children with HIV who cannot tolerate Trimethoprim/Sulfamethoxazole and can use a nebulizer. Intranvenous solutions of pentamidine should only be used in children with HIV older than 2 years old when other treatments are unavailable^[15]

Elderly

There is not data for the use of pentamidine in this specific population.^[14]

Contraindications

Patients with a history of anaphylaxis or hypersensitivity to pentamidine isethionate^[8]

Side effects

Common

Burning pain, dryness, or sensation of lump in throat
Chest pain
Coughing
difficulty in breathing
difficulty in swallowing
skin rash
wheezing^[16]

Rare

Nausea and vomiting
Pain in upper abdomen, possibly radiating to the back
Severe pain in side of chest
Shortness of breath^[16]

Others

Blood: Pentamidine frequently causes leukopenia and less often thrombopenia, which may cause symptomatic bleeding. Some cases of anemia, possibly related to folic acid deficiency, have been described.^[16]
Cardiovascular: Hypotension, which may be severe. Severe or fatal arrhythmias and heart failure are quite frequent.^[8]
Kidney: 25 percent develop signs of nephrotoxicity ranging from mild, asymptomatic azotemia (increased serum creatinine and urea) to irreversible renal failure. Ample fluids or intravenous hydration may prevent some nephrotoxicity.^[8]
Liver: Elevated liver enzymes are associated with intravenous use of pentamidine. Hepatomegaly and hepatitis have been encountered with long term prophylactic use of pentamidine inhalation.^[8]
Neurological: Dizziness, drowsiness, neuralgia, confusion, hallucinations, seizures and other central side effects are reported.^[8]
Pancreas: Hypoglycemia that requires symptomatic treatment is frequently seen. On the other hand, pentamidine may cause or worsen diabetes mellitus.^[8]
Respiratory: Cough and bronchospasm, most frequently seen with inhalation.^[8]
Skin: Severe local reactions after extravasculation of intravenous solutions or following intramuscular injection treatment have been seen. Pentamidine itself may cause rash, or rarely Stevens–Johnson syndrome or Lyell syndrome.^[8]
Eye discomfort, conjunctivitis, throat irritation, splenomegaly, Herxheimer reaction, electrolyte imbalances (e.g. hypocalcemia).^[8]

Drug interactions

The additional or sequential use of other nephrotoxic drugs like aminoglycosides, amphotericin B, capreomycin, colistin, polymyxin B, vancomycin, foscarnet, or cisplatin should be closely monitored, or whenever possible completely avoided.^[8]

Mechanism of action

The mechanism seems to vary with different organisms and is not well understood. However, pentamidine is suspected to work through various methods of interference of critical functions in DNA, RNA, phospholipid and protein synthesis.^[8]^[17] Pentamidine binds to adenine-thymine-rich regions of the Trypanosoma parasite DNA, forming a cross-link between two adenines four to five base pairs apart. The drug also inhibits topoisomerase enzymes in the mitochondria of Pneumocystis jirovecii. Similarly, pentamidine inhibits type II topoisomerase in the mitochondria of the Trypanosoma parasite, resulting in breaks and unraveling it's circular mitochondrial DNA.^[17]

Resistance

Strains of the Trypanosoma brucei parasite that are resistant to pentamidine have been discovered. Pentamidine is brought into the mitochondria through carriers, and the absence of these carriers prevents the drug from reaching its site of action.^[17]

Pharmacokinetics

Absorption: Pentamidine is completely absorbed when given intravenously or intramuscularly. When inhaled through a nebulizer, pentamidine accumulates in the bronchoalveolar fluid of the lungs at a higher concentration compared to injections. The inhaled form is minimally absorbed in the blood.^[9] Absorption is unreliable when given orally.^[10]

Distribution: When injected, pentamidine binds to tissues and proteins in the plasma. It accumulates in the kidney, liver, lungs, pancreas, spleen, and adrenal glands.^[18] Additionally, pentamidine does not reach curative levels in the cerebrospinal fluid.^[10] It has a volume of distribution of 286-1356 liters when given intravenously and 1658-3790 liters when given intramuscularly.^[19] Inhaled pentamidine is mainly deposited into the bronchoalveolar lavage fluid of the lungs.^[18]

Metabolism: Pentamidine is primarily metabolized by Cytochrome P450 enzymes in the liver.^[19]^[20] Up to 12% of pentamidine is eliminated in the urine unchanged.^[8]

Elimination: Pentamidine has an average half-life of 5–8 hours when given intravenously and 7–11 hours when given intramuscularly. However, these may increase with severe kidney problems.^[18] Pentamidine can remain in the system for as long as 8 months after the first injection.^[17]

Chemistry

Pentamidine isethionate for injection is commercially available as a lypophilized, white crystalline powder for reconstitution with sterile water or 5% Dextrose. After reconstitution, the mixture should be free from discoloration and precipitation. Reconstitution with sodium chloride should be avoided due to formation of precipitates. Intravenous solutions of pentamidine can be mixed with intravenous HIV medications like zidovidine and intravenous heart medications like diltiazem. However, intravenous solutions of antiviral foscarnet and antifungal fluconazole are incompatible with pentamidine.^[8] To avoid side-effects associated with intravenous administration, the solution should be slowly infused to minimize the release of histamine.^[17]

History

Pentamidine was first used to treat African trypanosomiasis in 1937 and leishmaniasis in 1940 before it was registered as pentamidine mesylate in 1950. Its efficacy against Pneumocystis jirovecii was demonstrated in 1987, following its re-emergence on the drug market in 1984 in the current isethionate form.^[10]

Trade names and dose form

For oral inhalation and for nebulizer use:^[7]

NebuPent Nebulizer (APP Pharmaceuticals LLC - US)

For intravenous and intramuscular use:^[7]

US and Canada:
- Pentacarinat 300 injection powder 300 mg vial (Avantis Pharma Inc - Canada)
- Pentam 300 (APP Pharmaceuticals LLC - US)
- Pentamidine isethionate 300 mg for injection (David Bull Laboratories LTD - Canada, Hospira Healthcare Corporation - Canada)
International Brands:^[7]
- Pentamidine isethionate (Abbott)
- Pentacarinat (Sanofi-Aventis)
- Pentacrinat (Abbott)
- Pentam (Abbott)
- Pneumopent

References

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k "Pentamidine Isethionate". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 3 December 2016.
^ "Pentamidine Use During Pregnancy". www.drugs.com. Archived from the original on 9 November 2016. Retrieved 3 December 2016.
^ Cohen, Jonathan; Powderly, William G.; Opal, Steven M. (2016). Infectious Diseases. Elsevier Health Sciences. p. 1368. ISBN 9780702063381. Archived from the original on 2017-03-08.
^ ^a ^b Magill, Alan J.; Strickland, G. Thomas; Maguire, James H.; Ryan, Edward T.; Solomon, Tom (2012). Hunter's Tropical Medicine and Emerging Infectious Disease (9 ed.). Elsevier Health Sciences. p. 723. ISBN 1455740438. Archived from the original on 2016-12-20.
^ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived (PDF) from the original on 13 December 2016. Retrieved 8 December 2016.
^ "Trypanosomiasis, human African (sleeping sickness)". World Health Organization. February 2016. Archived from the original on 4 December 2016. Retrieved 7 December 2016.
^ ^a ^b ^c ^d DrugBank, ed. (2016-08-17). "Pentamidine". DrugBank. Archived from the original on 2016-11-04.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ "DailyMed - PENTAM 300- pentamidine isethionate injection, powder, lyophilized, for solution". dailymed.nlm.nih.gov. Archived from the original on 2016-11-04. Retrieved 2016-11-07.
^ ^a ^b "DailyMed - NEBUPENT- pentamidine isethionate inhalant". dailymed.nlm.nih.gov. Archived from the original on 2016-11-04. Retrieved 2016-11-07.
^ ^a ^b ^c ^d ^e "Drugs". World Health Organization. Archived from the original on 2016-08-19. Retrieved 2016-11-04.
^ "Drugs@FDA: FDA Approved Drug Products". www.accessdata.fda.gov. Archived from the original on 2014-09-05. Retrieved 2016-11-07.
^ Lee MS, Johansen L, Zhang Y, et al. (December 2007). "The novel combination of chlorpromazine and pentamidine exerts synergistic antiproliferative effects through dual mitotic action". Cancer Res. 67 (23): 11359–67. doi:10.1158/0008-5472.CAN-07-2235. PMID 18056463.
^ Penumutchu, Srinivasa R.; Chou, Ruey-Hwang; Yu, Chin (2014-08-01). "Structural Insights into Calcium-Bound S100P and the V Domain of the RAGE Complex". PLOS ONE. 9 (8): e103947. doi:10.1371/journal.pone.0103947. ISSN 1932-6203. PMC 4118983 . PMID 25084534. Archived from the original on 2017-01-12.
^ ^a ^b ^c "Pentamidine Use During Pregnancy | Drugs.com". www.drugs.com. Archived from the original on 2016-11-09. Retrieved 2016-11-10.
^ "Pneumocystis jirovecii Pneumonia | Pediatric OI Prevention and Treatment Guidelines | AIDSinfo". AIDSinfo. Archived from the original on 2016-11-07. Retrieved 2016-11-07.
^ ^a ^b ^c "Pentamidine Side Effects in Detail - Drugs.com". www.drugs.com. Archived from the original on 2016-11-04. Retrieved 2016-11-04.
^ ^a ^b ^c ^d ^e Lemke, Thomas L.; Williams, David A., eds. (2013). Foye's Principles of Medicinal Chemistry (Seventh ed.). Philadelphia, PA: Lippincott Williams & Wilkins. ISBN 9781609133450.
^ ^a ^b ^c "Pentamidine (Oral Inhalation) (Professional Patient Advice) - Drugs.com". www.drugs.com. Archived from the original on 2016-11-04. Retrieved 2016-11-04.
^ ^a ^b "NebuPent, Pentam (pentamidine) dosing, indications, interactions, adverse effects, and more". reference.medscape.com. Archived from the original on 2016-11-06. Retrieved 2016-11-06.
^ Pubchem. "pentamidine | C19H24N4O2 - PubChem". pubchem.ncbi.nlm.nih.gov. Archived from the original on 2016-11-07. Retrieved 2016-11-06.

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. バベシア症：治療および予防 babesiosis treatment and prevention
2. 抗原虫治療 antiprotozoal therapies
3. アフリカトリパノソーマ症：臨床症状、診断、治療 african trypanosomiasis clinical manifestations diagnosis and treatment
4. HIV感染患者におけるニューモシスチス感染の治療および予防 treatment and prevention of pneumocystis infection in hiv infected patients
5. HIVに感染していない患者のニューモシスチス肺炎の治療と予防 treatment and prevention of pneumocystis pneumonia in hiv uninfected patients

English Journal

The inward rectifier current inhibitor PA-6 terminates atrial fibrillation and does not cause ventricular arrhythmias in goat and dog models.

Ji Y1, Varkevisser R1, Opacic D2, Bossu A1, Kuiper M2, Beekman JDM1, Yang S3, Khan AP4, Dobrev D4, Voigt N4,5,6, Wang MZ3, Verheule S2, Vos MA1, van der Heyden MAG1.
British journal of pharmacology.Br J Pharmacol.2017 Aug;174(15):2576-2590. doi: 10.1111/bph.13869. Epub 2017 Jun 28.
PMID 28542844

The establishment of in vitro culture and drug screening systems for a newly isolated strain of Trypanosoma equiperdum.

Suganuma K1, Yamasaki S2, Molefe NI3, Musinguzi PS4, Davaasuren B5, Mossaad E6, Narantsatsral S7, Battur B8, Battsetseg B9, Inoue N10.
International journal for parasitology. Drugs and drug resistance.Int J Parasitol Drugs Drug Resist.2017 Aug;7(2):200-205. doi: 10.1016/j.ijpddr.2017.04.002. Epub 2017 Apr 13.
PMID 28437733

The use of intravenous pentamidine for the prophylaxis of Pneumocystis pneumonia in pediatric patients.

Kruizinga MD1, Bresters D1, Smiers FJ1, Lankester AC1, Bredius RGM1.
Pediatric blood & cancer.Pediatr Blood Cancer.2017 Aug;64(8). doi: 10.1002/pbc.26453. Epub 2017 Jan 11.
PMID 28074607

Japanese Journal

治療に難渋したHIV感染症ニューモシスチス肺炎患者に対しアトバコン減感作療法が有効であった1症例

医療薬学 42(5), 373-380, 2016
NAID 130006855732

In Vitro Antiproliferative Effects of Several Diaryl Derivatives on Leishmania spp.

Biological & pharmaceutical bulletin 26(4), 453-456, 2003-04-01
NAID 110003608453

Vogt-小柳-原田病に対するステロイドパルス療法

日本眼科紀要 = Folia ophthalmologica Japonica 52(6), 471-474, 2001-06-28
NAID 10009737274

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★リンクテーブル★

リンク元	「ペンタミジン」
関連記事	「isethionate」

「ペンタミジン」

Pentamidine
Clinical data
Trade names	Nebupent, Pentam, others
Synonyms	pentamidine diisethionate, pentamidine dimesilate
AHFS/Drugs.com	Monograph
Pregnancy; category	US: C (Risk not ruled out) ; ;
Routes of; administration	IV, IM, inhalation
ATC code	P01CX01 (WHO) QP51AF02 (WHO);
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Protein binding	69%
Elimination half-life	6.4-9.4 hours
Identifiers
	IUPAC name 4,4'-[pentane-1,5-diylbis(oxy)]dibenzenecarboximidamide;
CAS Number	100-33-4 ;
PubChem CID	4735;
DrugBank	DB00738 ;
ChemSpider	4573 ;
UNII	673LC5J4LQ;
KEGG	D08333 ;
ChEBI	CHEBI:45081 ;
ChEMBL	CHEMBL55 ;
ECHA InfoCard	100.002.583
Chemical and physical data
Formula	C19H24N4O2
Molar mass	340.42 g/mol
3D model (JSmol)	Interactive image;
	SMILES O(c1ccc(cc1)C(=[N@H])N)CCCCCOc2ccc(C(=[N@H])N)cc2;
	InChI InChI=1S/C19H24N4O2/c20-18(21)14-4-8-16(9-5-14)24-12-2-1-3-13-25-17-10-6-15(7-11-17)19(22)23/h4-11H,1-3,12-13H2,(H3,20,21)(H3,22,23) ; Key:XDRYMKDFEDOLFX-UHFFFAOYSA-N ;
(verify)

　　[★]

英: pentamidine
化: イセチオン酸ペンタミジン, pentamidine isethionate
商: ベナンバックス

first aid step1 2006 p.147,173,178

分類

カリニ肺炎治療薬。

構造

薬効薬理

ベナンバックス注用300mg

1. ペンタミジンイセチオン酸塩は、in vitroにおいて、カリニ肺炎発症ラットの肺より分離されたニューモシスチス・カリニに対して、致死的作用を有することが示唆された。
2. ペンタミジンイセチオン酸塩はin vitroでニューモシスチス・カリニのグルコース代謝及び蛋白質合成を抑制し、マウス実験腫瘍のDNA合成、RNA合成、蛋白質合成、リン脂質合成及びヌクレオチド合成を抑制し、ジヒドロ葉酸脱水素酵素（DHFR）活性をin vitro及びin vivo（ラット）で抑制した

投与方法

静脈投与・筋肉内投与
吸入投与

適応

カリニ肺炎

注意

ベナンバックス注用300mg

重篤な低血圧、低血糖及び不整脈があらわれることがある。用法及び用量、使用上の注意に特に留意し、このような症状が発現した場合は直ちに本薬の投与を中止し、再投与しないこと。

禁忌

ベナンバックス注用300mg

1. 本剤に対する過敏症の既往歴のある患者
2. ザルシタビンを投与中の患者［海外で本剤（静注）との併用により劇症膵炎による死亡例が報告されているので、カリニ肺炎の治療のため本剤が必要になった場合は、ザルシタビンを休薬すること。「3.相互作用」の項参照］
3. ホスカルネットナトリウムを投与中の患者［腎障害の増強、低カルシウム血症が起こることがある。なお、海外で本剤（静注）との併用により、重篤な低カルシウム血症が発現した死亡例が報告されている。「3.相互作用」の項参照］
4. 吸入投与は、換気障害が重症の患者（PaO2 60mmHg以下）には行わないこと。［換気障害のため、薬剤の十分な拡散が得られないことがある。］
5. アミオダロン（注射剤）を投与中の患者［併用によりTorsades de pointesのリスクが増加する。「3.相互作用」の項参照］

副作用

添付文書

ベナンバックス注用300mg

http://www.info.pmda.go.jp/go/pack/6419400D1037_1_02/6419400D1037_1_02?view=body

「isethionate」

　　[★]

イセチオン酸、イセチオン酸塩

関: isethionic acid

[AHFS2016-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k "Pentamidine Isethionate". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 3 December 2016.

[2] "Pentamidine Use During Pregnancy". www.drugs.com. Archived from the original on 9 November 2016. Retrieved 3 December 2016.

[3] Cohen, Jonathan; Powderly, William G.; Opal, Steven M. (2016). Infectious Diseases. Elsevier Health Sciences. p. 1368. ISBN 9780702063381. Archived from the original on 2017-03-08.

[Mag2012-4] Magill, Alan J.; Strickland, G. Thomas; Maguire, James H.; Ryan, Edward T.; Solomon, Tom (2012). Hunter's Tropical Medicine and Emerging Infectious Disease (9 ed.). Elsevier Health Sciences. p. 723. ISBN 1455740438. Archived from the original on 2016-12-20.

[WHO19th-5] "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived (PDF) from the original on 13 December 2016. Retrieved 8 December 2016.

[WHO2016-6] "Trypanosomiasis, human African (sleeping sickness)". World Health Organization. February 2016. Archived from the original on 4 December 2016. Retrieved 7 December 2016.

[Bank2016-7] DrugBank, ed. (2016-08-17). "Pentamidine". DrugBank. Archived from the original on 2016-11-04.

[:10-8] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ "DailyMed - PENTAM 300- pentamidine isethionate injection, powder, lyophilized, for solution". dailymed.nlm.nih.gov. Archived from the original on 2016-11-04. Retrieved 2016-11-07.

[:11-9] "DailyMed - NEBUPENT- pentamidine isethionate inhalant". dailymed.nlm.nih.gov. Archived from the original on 2016-11-04. Retrieved 2016-11-07.

[:1-10] "Drugs". World Health Organization. Archived from the original on 2016-08-19. Retrieved 2016-11-04.

[11] "Drugs@FDA: FDA Approved Drug Products". www.accessdata.fda.gov. Archived from the original on 2014-09-05. Retrieved 2016-11-07.

[pmid18056463-12] Lee MS, Johansen L, Zhang Y, et al. (December 2007). "The novel combination of chlorpromazine and pentamidine exerts synergistic antiproliferative effects through dual mitotic action". Cancer Res. 67 (23): 11359–67. doi:10.1158/0008-5472.CAN-07-2235. PMID 18056463.

[13] Penumutchu, Srinivasa R.; Chou, Ruey-Hwang; Yu, Chin (2014-08-01). "Structural Insights into Calcium-Bound S100P and the V Domain of the RAGE Complex". PLOS ONE. 9 (8): e103947. doi:10.1371/journal.pone.0103947. ISSN 1932-6203. PMC 4118983 . PMID 25084534. Archived from the original on 2017-01-12.

[:12-14] "Pentamidine Use During Pregnancy | Drugs.com". www.drugs.com. Archived from the original on 2016-11-09. Retrieved 2016-11-10.

[:8-15] "Pneumocystis jirovecii Pneumonia | Pediatric OI Prevention and Treatment Guidelines | AIDSinfo". AIDSinfo. Archived from the original on 2016-11-07. Retrieved 2016-11-07.

[:4-16] "Pentamidine Side Effects in Detail - Drugs.com". www.drugs.com. Archived from the original on 2016-11-04. Retrieved 2016-11-04.

[:6-17] Lemke, Thomas L.; Williams, David A., eds. (2013). Foye's Principles of Medicinal Chemistry (Seventh ed.). Philadelphia, PA: Lippincott Williams & Wilkins. ISBN 9781609133450.

[:2-18] "Pentamidine (Oral Inhalation) (Professional Patient Advice) - Drugs.com". www.drugs.com. Archived from the original on 2016-11-04. Retrieved 2016-11-04.

[:7-19] "NebuPent, Pentam (pentamidine) dosing, indications, interactions, adverse effects, and more". reference.medscape.com. Archived from the original on 2016-11-06. Retrieved 2016-11-06.

[20] Pubchem. "pentamidine | C19H24N4O2 - PubChem". pubchem.ncbi.nlm.nih.gov. Archived from the original on 2016-11-07. Retrieved 2016-11-06.

v t e Ionotropic glutamate receptor modulators
AMPAR	Agonists: Main site agonists: 5-Fluorowillardiine Acromelic acid (acromelate) AMPA BOAA Domoic acid Glutamate Ibotenic acid Proline Quisqualic acid Willardiine; Positive allosteric modulators: Aniracetam BIIB-104 (PF-04958242) Cyclothiazide CX-516 CX-546 CX-614 Farampator (CX-691, ORG-24448) CX-717 CX-1739 CX-1942 Diazoxide Hydrochlorothiazide (HCTZ) IDRA-21 LY-392098 LY-395153 LY-404187 LY-451646 LY-503430 Mibampator (LY-451395) Nooglutyl ORG-26576 Oxiracetam PEPA Piracetam Pramiracetam S-18986 Tulrampator (S-47445, CX-1632) Antagonists: ACEA-1011 ATPO Becampanel Caroverine CNQX Dasolampanel DNQX Fanapanel (MPQX) GAMS Kaitocephalin Kynurenic acid Kynurenine Licostinel (ACEA-1021) NBQX PNQX Selurampanel Tezampanel Theanine Topiramate YM90K Zonampanel; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental) Cyclopropane Enflurane Ethanol (alcohol) Evans blue GYKI-52466 GYKI-53655 Halothane Irampanel Isoflurane Perampanel Pregnenolone sulfate Sevoflurane Talampanel; Unknown/unsorted antagonists: Minocycline
KAR	Agonists: Main site agonists: 5-Bromowillardiine 5-Iodowillardiine Acromelic acid (acromelate) AMPA ATPA Domoic acid Glutamate Ibotenic acid Kainic acid LY-339434 Proline Quisqualic acid SYM-2081; Positive allosteric modulators: Cyclothiazide Diazoxide Enflurane Halothane Isoflurane Antagonists: ACEA-1011 CNQX Dasolampanel DNQX GAMS Kaitocephalin Kynurenic acid Licostinel (ACEA-1021) LY-382884 NBQX NS102 Selurampanel Tezampanel Theanine Topiramate UBP-302; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental) Enflurane Ethanol (alcohol) Evans blue NS-3763 Pregnenolone sulfate
NMDAR	Agonists: Main site agonists: AMAA Aspartate Glutamate Homocysteic acid (L-HCA) Homoquinolinic acid Ibotenic acid NMDA Proline Quinolinic acid Tetrazolylglycine Theanine; Glycine site agonists: β-Fluoro-D-alanine ACBD ACC (ACPC) ACPD AK-51 Apimostinel (NRX-1074) B6B21 CCG D-Alanine D-Cycloserine D-Serine DHPG Dimethylglycine Glycine HA-966 L-687414 L-Alanine L-Serine Milacemide Neboglamine (nebostinel) Rapastinel (GLYX-13) Sarcosine; Polyamine site agonists: Neomycin Spermidine Spermine; Other positive allosteric modulators: 24S-Hydroxycholesterol DHEA (prasterone) DHEA sulfate (prasterone sulfate) Epipregnanolone sulfate Pregnenolone sulfate SAGE-201 SAGE-301 SAGE-718 Antagonists: Competitive antagonists: AP5 (APV) AP7 CGP-37849 CGP-39551 CGP-39653 CGP-40116 CGS-19755 CPP Kaitocephalin LY-233053 LY-235959 LY-274614 MDL-100453 Midafotel (d-CPPene) NPC-12626 NPC-17742 PBPD PEAQX Perzinfotel PPDA SDZ-220581 Selfotel; Glycine site antagonists: 4-Cl-KYN (AV-101) 5,7-DCKA 7-CKA ACC ACEA-1011 ACEA-1328 Apimostinel (NRX-1074) AV-101 Carisoprodol CGP-39653 CNQX D-Cycloserine DNQX Felbamate Gavestinel GV-196771 Harkoseride Kynurenic acid Kynurenine L-689560 L-701324 Licostinel (ACEA-1021) LU-73068 MDL-105519 Meprobamate MRZ 2/576 PNQX Rapastinel (GLYX-13) ZD-9379; Polyamine site antagonists: Arcaine Co 101676 Diaminopropane Diethylenetriamine Huperzine A Putrescine; Uncompetitive pore blockers (mostly dizocilpine site): 2-MDP 3-HO-PCP 3-MeO-PCE 3-MeO-PCMo 3-MeO-PCP 4-MeO-PCP 8A-PDHQ 18-MC α-Endopsychosin Alaproclate Alazocine (SKF-10047) Amantadine Aptiganel Argiotoxin-636 Arketamine ARL-12495 ARL-15896-AR ARL-16247 Budipine Coronaridine Delucemine (NPS-1506) Dexoxadrol Dextrallorphan Dextromethadone Dextromethorphan Dextrorphan Dieticyclidine Diphenidine Dizocilpine Ephenidine Esketamine Etoxadrol Eticyclidine Fluorolintane Gacyclidine Ibogaine Ibogamine Indantadol Ketamine Ketobemidone Lanicemine Levomethadone Levomethorphan Levomilnacipran Levorphanol Loperamide Memantine Methadone Methorphan Methoxetamine Methoxphenidine Milnacipran Morphanol NEFA Neramexane Nitromemantine Noribogaine Norketamine Orphenadrine PCPr PD-137889 Pethidine (meperidine) Phencyclamine Phencyclidine Propoxyphene Remacemide Rhynchophylline Rimantadine Rolicyclidine Sabeluzole Tabernanthine Tenocyclidine Tiletamine Tramadol; Ifenprodil (NR2B) site antagonists: Besonprodil Buphenine (nylidrin) CO-101244 (PD-174494) Eliprodil Haloperidol Isoxsuprine Radiprodil (RGH-896) Rislenemdaz (CERC-301, MK-0657) Ro 8-4304 Ro 25-6981 Safaprodil Traxoprodil (CP-101606); NR2A-selective antagonists: MPX-004 MPX-007 TCN-201 TCN-213; Cations: Hydrogen Magnesium Zinc; Alcohols/volatile anesthetics/related: Benzene Butane Chloroform Cyclopropane Desflurane Diethyl ether Enflurane Ethanol (alcohol) Halothane Hexanol Isoflurane Methoxyflurane Nitrous oxide Octanol Sevoflurane Toluene Trichloroethane Trichloroethanol Trichloroethylene Urethane Xenon Xylene; Unknown/unsorted antagonists: ARR-15896 Bumetanide Caroverine Conantokin D-αAA Dexanabinol Flufenamic acid Flupirtine FPL-12495 FR-115427 Furosemide Hodgkinsine Ipenoxazone (MLV-6976) MDL-27266 Metaphit Minocycline MPEP Niflumic acid Pentamidine Pentamidine isethionate Piretanide Psychotridine Transcrocetin (saffron) Unsorted: Allosteric modulators: AGN-241751
See also: Receptor/signaling modulators Metabotropic glutamate receptor modulators Glutamate metabolism/transport modulators

Clinical data


Trade names	Nebupent, Pentam, others^[1]
Synonyms	pentamidine diisethionate, pentamidine dimesilate
AHFS/Drugs.com	Monograph
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	IV, IM, inhalation
ATC code	P01CX01 (WHO) QP51AF02 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding	69%
Elimination half-life	6.4-9.4 hours
Identifiers
IUPAC name 4,4'-[pentane-1,5-diylbis(oxy)]dibenzenecarboximidamide
CAS Number	100-33-4^Y
PubChem CID	4735
DrugBank	DB00738^Y
ChemSpider	4573^Y
UNII	673LC5J4LQ
KEGG	D08333^Y
ChEBI	CHEBI:45081^Y
ChEMBL	CHEMBL55^Y
ECHA InfoCard	100.002.583
Chemical and physical data
Formula	C₁₉H₂₄N₄O₂
Molar mass	340.42 g/mol
3D model (JSmol)	Interactive image
SMILES O(c1ccc(cc1)C(=[N@H])N)CCCCCOc2ccc(C(=[N@H])N)cc2
InChI InChI=1S/C19H24N4O2/c20-18(21)14-4-8-16(9-5-14)24-12-2-1-3-13-25-17-10-6-15(7-11-17)19(22)23/h4-11H,1-3,12-13H2,(H3,20,21)(H3,22,23)^Y Key:XDRYMKDFEDOLFX-UHFFFAOYSA-N^Y
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