acitretin

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/07/12 18:19:18」(JST)

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Acitretin

Systematic (IUPAC) name
(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
Clinical data
Trade names	Soriatane
AHFS/Drugs.com	monograph
MedlinePlus	a601010
Pregnancy cat.	X
Legal status	?
Pharmacokinetic data
Bioavailability	60%
Protein binding	99%
Half-life	49 hours
Identifiers
CAS number	55079-83-9 Y
ATC code	D05BB02
PubChem	CID 5284513
DrugBank	DB00459
ChemSpider	4447573 Y
UNII	LCH760E9T7 Y
KEGG	D02754 Y
ChEBI	CHEBI:50173 Y
ChEMBL	CHEMBL1131 Y
Chemical data
Formula	C21H26O3
Mol. mass	326.429 g/mol
SMILES O=C(O)\C=C(\C=C\C=C(\C=C\c1c(cc(OC)c(c1C)C)C)C)C
InChI InChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12+ Y Key:IHUNBGSDBOWDMA-AQFIFDHZSA-N Y
Y (what is this?)  (verify)

Acitretin (trade name Soriatane or Neotigason) is a second-generation retinoid. It is taken orally, and is typically used for psoriasis.

It is a metabolite of etretinate, which was used prior to the introduction of acitretin. Etretinate was discontinued because it had a narrow therapeutic index as well as a long elimination half-life (t_1/2=120 days), making dosing difficult. In contrast, acitretin's half-life is approximately 2 days. However, because acitretin can be reverse metabolised into etretinate which has an extremely long half-life, women must avoid becoming pregnant for at least 3 years after discontinuing acitretin. Therefore, acitretin is generally not recommended for women of child-bearing age with a risk of becoming pregnant.

Acitretin is an oral retinoid used in the treatment of severe resistant psoriasis. Because of the potential for problems and severe side effects it is generally used in only very severe cases of psoriasis that have been unresponsive to other treatments. It binds to nuclear receptors that regulates gene transcription. They induce keratinocyte differentiation and reduce epidermal hyperplasia, leading to the slowing of cell reproduction. Acitretin is readily absorbed and widely distributed after oral administration. A therapeutic effect occurs after 2 to 4 weeks or longer.

Patients that have received the medication are advised against giving blood for at least 3 years due to the risk of birth defects.

Side Effects

Acitretin is noted for the possibility of severe birth defects and should not be used by pregnant women or women planning to get pregnant within 3 years following the use of Acitretin. Sexually active women of childbearing age who use Acitretin should also use at least 2 forms of birth control concurrently. Men and women who use it should not donate blood for 3 years after using it, because of the possibility that the blood might be used in a pregnant patient and cause birth defects. In addition, it may cause nausea, headache, itching, dry, red or flaky skin, dry or red eyes, dry or chapped lips, dry mouth, thirst or hair loss Many other side effects have also been reported.

References

UpToDate Contents

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• 1. 膿疱性乾癬：マネージメント pustular psoriasis management
• 2. 特殊集団における、中等症から重症の局面型乾癬に対する治療選択 treatment selection for moderate to severe plaque psoriasis in special populations
• 3. 毛孔性紅色粃糠疹 pityriasis rubra pilaris
• 4. 実質臓器移植受容者における皮膚癌のマネージメント management of skin cancer in solid organ transplant recipients
• 5. 妊婦における乾癬のマネージメント management of psoriasis in pregnant women

English Journal

• Drug fever as an adverse effect of acitretin in complicated psoriasis patient.

• Rob F1, Fialová J1, Brejchová M1, Džambová M1, Sečníková Z1, Zelenková D1, Jiráková A1, Hercogová J1.
• Dermatologic therapy.Dermatol Ther.2015 Jul 2. doi: 10.1111/dth.12263. [Epub ahead of print]
• We present a case of a 63-year old man with severe chronic plaque psoriasis and a recent history of lung cancer, wherein fever appeared suddenly after initiation of treatment with low dose acitretin. Tumor recurrence or infection was not found during extensive examinations, nevertheless the patient
• PMID 26133643

• Deep Fungal Infections, Blastomycosis-Like Pyoderma, and Granulomatous Sexually Transmitted Infections.

• Guidry JA1, Downing C2, Tyring SK3.
• Dermatologic clinics.Dermatol Clin.2015 Jul;33(3):595-607. doi: 10.1016/j.det.2015.03.019.
• Granulomatous diseases are caused by multiple infectious and noninfectious causes. Deep fungal infections can present in the skin or extracutaneously, most commonly with lung manifestations. An Azole or amphotericin B is the universal treatment. Blastomycosis-like pyoderma is a clinically similar co
• PMID 26143434

• Serum Sirolimus Level Elevation Induced by Acitretin: Report of a Novel Drug-Drug Interaction.

• Rossi AM, Hibler BP, Johnson-Jahangir H.
• Journal of drugs in dermatology : JDD.J Drugs Dermatol.2015 Jul 1;14(7):747-9.
• Long-term immunosuppression in the organ transplant recipient (OTR) population places these individuals at higher risk of developing skin malignancies. Oral retinoids have become a useful tool for pharmacologic prophylaxis in the OTR population. Immunosuppressants that inhibit mTOR, such as sirolimu
• PMID 26151793

Japanese Journal

• Keratosis lichenoides chronica treated with acitretin plus narrowband ultraviolet B phototherapy

• KOSEOGLU Resit Dogan,SEZER Engin,YUKSEK Jale
• Journal of dermatology 35(3), 172-174, 2008-03-01
• NAID 10021307425

• Acitretin induced bipedal edema

• TEY Hong Liang,THENG Thiam Seng Colin
• Journal of dermatology 33(5), 372-374, 2006-05-01
• NAID 10020340329

• Imatinib-associated lichenoid eruption : acitretin treatment allows maintained antineoplastic effect

• DALMAU J
• Br J Dermatol 154, 1213-1216, 2006
• NAID 30014639986

Related Links

• Acitretinとは - goo Wikipedia (ウィキペディア)

Acitretin (trade name Soriatane or Neotigason) is a second-generation retinoid. It is taken orally, and is typically used for psoriasis. It is a metabolite of etretinate, which was used prior to the introduction of acitretin. Etretinate was ...

• Acitretin: MedlinePlus Drug Information - National Library of ...

Before taking acitretin, tell your doctor and pharmacist if you have had a serious allergic reaction (difficulty breathing or swallowing, hives, itching, or swelling of the face, throat, tongue, lips, or eyes) to acitretin, other ...

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