pentazocine hydrochloride

塩酸ペンタゾシン

WordNet

1. a complex consisting of an organic base in association with hydrogen chloride
2. analgesic drug (trade name Talwin) that is less addictive than morphine (同)Talwin

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/09/28 18:21:01」(JST)

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Pentazocine

Clinical data
Pregnancy category	AU: C US: C (Risk not ruled out) or D (if used near to term)
Routes of administration	Oral, IV, IM
ATC code	N02AD01 (WHO)
Legal status
Legal status	AU: S8 (Controlled) CA: Schedule I DE: Anlage III (Special prescription form required) US: Schedule IV
Pharmacokinetic data
Bioavailability	~20% orally
Metabolism	Hepatic
Onset of action	15 min
Biological half-life	2 to 3 hours
Excretion	Renal
Identifiers
IUPAC name (2RS,6RS,11RS)-6,11-dimethyl-3-(3-methylbut-2-en-1-yl)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-8-ol or 2-dimethylallyl-5,9-dimethyl-2'-hydroxybenzomorphan
CAS Number	359-83-1 Y
PubChem CID	441278
IUPHAR/BPS	1606
DrugBank	DB00652 Y
ChemSpider	390041 Y
UNII	RP4A60D26L
KEGG	D00498 Y
ChEMBL	CHEMBL560 Y
ECHA InfoCard	100.006.032
Chemical and physical data
Formula	C19H27NO
Molar mass	285.424 g/mol
3D model (JSmol)	Interactive image
SMILES Oc1ccc3c(c1)[C@]2([C@H]([C@H](N(CC2)C\C=C(/C)C)C3)C)C
InChI InChI=1S/C19H27NO/c1-13(2)7-9-20-10-8-19(4)14(3)18(20)11-15-5-6-16(21)12-17(15)19/h5-7,12,14,18,21H,8-11H2,1-4H3/t14-,18+,19+/m0/s1 Y Key:VOKSWYLNZZRQPF-GDIGMMSISA-N Y
(verify)

Pentazocine, sold under the brand name Talwin among others, is a painkiller used to treat moderate to severe pain. It is believed to work by activating (agonizing) κ-opioid receptors (KOR) and blocking (antagonizing) μ-opioid receptors (MOR). As such it is called an opioid as it delivers its effects on pain by interacting with the opioid receptors. It shares many of the side effects of other opioids like constipation, nausea, itching, drowsiness and a reduced effort to breathe, but unlike most other opioids it fairly frequently causes hallucinations, nightmares and delusions. It is also, unlike most other opioids, subject to a ceiling effect, which is when at a certain dose (which differs from person-to-person) no more pain relief, or side effects, is obtained by increasing the dose any further.

Chemically it is classed as a benzomorphan and it comes in two enantiomers, which are molecules that are exact mirror images of one another.

Usually, in its oral formulations, it is combined with naloxone so as to prevent people from crushing the tablets, dissolving them in a solvent (like water) and injecting them for a high (as naloxone, if taken by mouth, produces no effects. If injected, however, it does).

Use

Medical

Pentazocine is used primarily to treat pain, although its analgesic effects are subject to a ceiling effect. It has been discontinued by its corporate sponsor in Australia, although it may be available through the special access scheme.

Recreational

In the 1970s, recreational drug users discovered that combining pentazocine with tripelennamine (a first-generation ethylenediamine antihistamine most commonly dispensed under the brand names Pelamine and Pyribenzamine) produced a euphoric sensation. Since tripelennamine tablets are typically blue in color and brand-name Pentazocine is known as Talwin (hence "Ts"), the pentazocine/tripelennamine combination acquired the slang name Ts and blues. After health-care professionals and drug-enforcement officials became aware of this scenario, the mu-opioid-antagonist naloxone was added to oral preparations containing pentazocine to prevent perceived "misuse" via injection, and the reported incidence of its recreational use has declined precipitously since.

Research

In an open-label, add-on, single-day, acute-dose small clinical study, pentazocine was found to rapidly and substantially reduce symptoms of mania in individuals with bipolar disorder that were in the manic phase of the condition. It was postulated that the efficacy observed was due to κ-opioid receptor activation-mediated amelioration of hyperdopaminergia in the reward pathways. Minimal sedation and no side effects including psychotomimetic effects or worsening of psychosis were observed at the dose administered.

Adverse effects

Side effects are similar to those of morphine, but pentazocine, due to its action at the kappa opioid receptor is more likely to invoke psychotomimetic effects. High dose may cause high blood pressure or high heart rate. It may also increase cardiac work after myocardial infarction when given intravenously and hence this use should be avoided where possible. Respiratory depression is a common side effect, but is subject to a ceiling effect, such that at a certain dose the degree of respiratory depression will no longer increase with dose increases. Likewise rarely it has been associated with agranulocytosis, erythema multiforme and toxic epidermal necrolysis.

Tissue damage at injection sites

Severe injection site necrosis and sepsis has occurred (sometime requiring amputation of limb) with multiple injection of pentazocine lactate. In addition, animal studies have demonstrated that Pentazocine is tolerated less well subcutaneously than intramuscularly.

History

Pentazocine was developed by the Sterling Drug Company, Sterling-Winthrop Research Institute, of Rensselaer, New York. It was approved by the Food and Drug Administration in June 1967 after being favorably reviewed following testing on 12,000 patients in the United States. The analgesic compound was first made at Sterling in 1958. U.S. testing was conducted between 1961 and 1967. By mid 1967 Pentazocine was already being sold in Mexico, England, and Argentina, under different trade names.

Society and culture

Legal status

Pentazocine was originally classified in Schedule V under the Controlled Substances Act but a petition was filed with the D.E.A. on October 1, 1971, to shift it to Schedule III. The petition was filed by Joseph L. Fink III, a pharmacist and law student at Georgetown University Law Center as part of the course Lawyering in the Public Interest. That petition was accepted for review on November 10, 1971 D.E.A. published a Final Rule transferring it to schedule IV on January 10, 1979, with an effective date of February 9, 1979 This is understood to be the first instance of a successful petition to reclassify a substance under the relatively recently enacted Controlled Substances Act. Pentazocine is still classified in Schedule IV under the Controlled Substances Act in the United States, even with the addition of Naloxone. although some states classify it in Schedule III. Internationally, pentazocine is a Schedule III drug under the Convention on Psychotropic Substances. Pentazocine has a DEA ACSCN of 9720; being a Schedule IV substance, the DEA does not assign an annual manufacturing quota for pentazocine for the United States.

Brand names

Pentazocine is sold under several brand names, such as Fortral, Sosegon, Talwin NX (with naloxone), Talwin, Talwin PX, Fortwin and Talacen (with paracetamol (acetaminophen)).

See also

• Cyclazocine (hallucinogenic)
• Volazocine

External links

• Eurekalert report on PNAS article

UpToDate Contents

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English Journal

• Pharmacological profiling of sigma 1 receptor ligands by novel receptor homomer assays.

• Yano H1, Bonifazi A2, Xu M3, Guthrie DA2, Schneck SN4, Abramyan AM3, Fant AD3, Hong WC4, Newman AH2, Shi L5.
• Neuropharmacology.Neuropharmacology.2018 Jan 30. pii: S0028-3908(18)30048-0. doi: 10.1016/j.neuropharm.2018.01.042. [Epub ahead of print]
• PMID 29407216

• Efficacy and safety of sedation during endoscopic submucosal dissection of gastric cancers using a comparative trial of propofol versus midazolam.

• Kikuchi H1,2, Hikichi T1, Watanabe K1,2, Nakamura J1,2, Takagi T2, Suzuki R2, Sugimoto M2, Waragai Y2, Konno N2, Asama H2, Takasumi M2, Sato Y2, Obara K3, Ohira H2.
• Endoscopy international open.Endosc Int Open.2018 Jan;6(1):E51-E57. doi: 10.1055/s-0043-122225. Epub 2018 Jan 12.
• PMID 29340298

• Usefulness of Consciousness Sedation with Dexmedetomidine and Pentazocine during Endovascular Treatment for Acute Stroke.

• Nii K1, Hanada H1, Hiraoka F1, Eto A1, Mitsutake T1, Tsutsumi M1.
• Neurologia medico-chirurgica.Neurol Med Chir (Tokyo).2017 Dec 19. doi: 10.2176/nmc.oa.2017-0188. [Epub ahead of print]
• PMID 29269633

Japanese Journal

• 胸腔鏡下肺切除術後疼痛管理における持続傍脊椎神経ブロックの有用性に関する検討

• 日本呼吸器外科学会雑誌 = The journal of the Japanese Association for Chest Surgery 26(4), 373-379, 2012-05-15
• NAID 10030435542

• 斜角筋間腕神経叢ブロックによる肩関節鏡手術

• 肩関節 35(2), 633-635, 2011
• NAID 130001413768

• 国立駿河療養所におけるハンセン病由来の神経因性疼痛に対する医薬品使用の動向 : 1998年から2008年にかけて

• 日本ハンセン病学会雑誌 = Japanese journal of leprosy 78(3), 293-296, 2009-09-01
• NAID 10026085024

Related Links

• Pentazocine Hydrochloride Monograph for Professionals ...

Pentazocine Hydrochloride reference guide for safe and effective use from the American Society of Health-System Pharmacists (AHFS DI). ... Cautions for Pentazocine Hydrochloride Contraindications Known hypersensitivity to ...

• Pentazocine hydrochloride | definition of pentazocine ...

pentazocine hydrochloride [pentā′zəsēn] an agonist/antagonist opioid analgesic that stimulates kappa opioid receptors and blocks the mu opioid receptors. Also called pentazocine lactate. indication It is prescribed for the relief of ...

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★リンクテーブル★

リンク元	「ペンタゾシン」
関連記事	「hydrochloride」

「ペンタゾシン」

　　[★]

英

pentazocine

ラ

pentazocinum

化

塩酸ペンタゾシン pentazocine hydrochloride

商

ソセゴン Sosegon(アステラス)、ペンタジン Pentagin(第一三共)、ペルタゾン、Talwin

関

全身麻酔薬、拮抗性麻酔薬

• 全身麻酔薬

• 拮抗性麻酔薬

作用機序

• μ受容体に対する部分作動薬、κ受容体の全てに対する作動薬であり、κ受容体を通じて麻酔作用を示す。

利点

• 胆道閉塞性疾患にも慎重に使用できる(ブプレノルフィンは慎重投与だがペンタゾシンの大量投与は慎重) μ2受容体がOddi筋収縮に関わるとされている。

「hydrochloride」

　　[★] 塩酸塩、ハイドロクロライド