Siproteron asetat

Siproteron asetat
Nama sistematis (IUPAC)
	(2aR,3aS,3bS,3cS,5aS,6R,8aS,8bR)-6-asetil-10-kloro-3b,5a-dimetil-2-okso-2,2a,3,3a,3b,3c,4,5,5a,6,7,8,8a,8b-tetradekahidrosiklopenta[a]siklopropa[g]fenantren-6-il asetat
Data klinis
Nama dagang	Androcur, Androcur Depot, Cyprostat, Siterone, dll
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Kat. kehamilan	X
Status hukum	℞ Preskripsi saja
Rute	Oral, intramuskular
Data farmakokinetik
Bioavailabilitas	Oral: 68–100%
Ikatan protein	Albumin: 93%; Bebas: 7%
Metabolisme	Hati (CYP3A4)
Waktu paruh	Oral: 1,6–4,3 hari; IM: 3–4,3 hari
Ekskresi	Feses: 70%; Urin: 30%
Pengenal
Nomor CAS	427-51-0 ; 2098-66-0 (Alkohol bebas)
Kode ATC	G03HA01
PubChem	CID 9880
Ligan IUPHAR	2865
DrugBank	DB04839
ChemSpider	9496
UNII	4KM2BN5JHF
KEGG	D01368
ChEBI	CHEBI:50743
ChEMBL	CHEMBL139835
Sinonim	SH-80714; SH-714; NSC-81430; 1α,2α-Metilena-6-kloro-17α-hidroksi-δ6-progesteron asetate; 1α,2α-Metilena-6-kloro-17α-hidroksipregna-4,6-diena-3,20-diona asetat
Data kimia
Rumus	C24H29ClO4
	InChI InChI=1S/C24H29ClO4/c1-12(26)24(29-13(2)27)8-6-16-14-10-20(25)19-11-21(28)18(15)23(19,4)17(14)5-7-22(16,24)3/h10-11,14-18H,5-9H2,1-4H3/t14-,15+,16-,17-,18-,22-,23-,24-/m0/s1; Key:UWFYSQMTEOIJJG-FDTZYFLXSA-N;
Data fisik
Titik lebur	200–201 °C (392–394 °F)

Siproteron asetat (bahasa Inggris: Cyproterone acetate, disingkat CPA), dijual sendiri dengan merek Androcur atau bersama dengan etinilestradiol dengan merek Diane atau Diane-35, adalah obat antiandrogen dan progestin yang digunakan dalam pengobatan kondisi yang bergantung pada androgen seperti jerawat, hirsutisme, pubertas dini, dan kanker prostat, serta sebagai komponen Terapi hormon feminin untuk individu transgender, dan dalam pil KB.^[1]^[10]^[12]^[13]^[14] Obat ini diformulasikan dan digunakan baik sendiri maupun dalam kombinasi dengan estrogen. CPA diminum satu hingga tiga kali sehari.

Referensi

^ ^a ^b Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947.
^ ^a ^b Huber J, Zeillinger R, Schmidt J, Täuber U, Kuhnz W, Spona J (November 1988). "Pharmacokinetics of cyproterone acetate and its main metabolite 15 beta-hydroxy-cyproterone acetate in young healthy women". International Journal of Clinical Pharmacology, Therapy, and Toxicology. 26 (11): 555–561. PMID 2977383.
^ Bińkowska M, Woroń J (June 2015). "Progestogens in menopausal hormone therapy". Przeglad Menopauzalny = Menopause Review. 14 (2): 134–143. doi:10.5114/pm.2015.52154. PMC 4498031 . PMID 26327902.
^ Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH (December 2003). "Classification and pharmacology of progestins". Maturitas. 46 Suppl 1 (Suppl 1): S7–S16. doi:10.1016/j.maturitas.2003.09.014. PMID 14670641. Since there is no binding of CPA to SHBG and CBG in the serum, 93% of the compound is bound to serum albumin.
^ Wakelin SH, Maibach HI, Archer CB (1 June 2002). Systemic Drug Treatment in Dermatology: A Handbook. CRC Press. hlm. 32–. ISBN 978-1-84076-013-2. Diarsipkan dari versi asli tanggal 14 January 2023. Diakses tanggal 27 September 2016. It is almost exclusively bound to plasma albumin.
^ Hammond GL, Lähteenmäki PL, Lähteenmäki P, Luukkainen T (October 1982). "Distribution and percentages of non-protein bound contraceptive steroids in human serum". Journal of Steroid Biochemistry. 17 (4): 375–380. doi:10.1016/0022-4731(82)90629-X. PMID 6215538.
^ Dickman A (27 September 2012). Drugs in Palliative Care. OUP Oxford. hlm. 137–138. ISBN 978-0-19-966039-1.
^ Boarder M, Newby D, Navti P (25 March 2010). Pharmacology for Pharmacy and the Health Sciences: A Patient-centred Approach. OUP Oxford. hlm. 632–. ISBN 978-0-19-955982-4. Diarsipkan dari versi asli tanggal 6 July 2024. Diakses tanggal 27 September 2016.
^ ^a ^b ^c ^d Weber GF (22 July 2015). Molecular Therapies of Cancer. Springer. hlm. 316–. ISBN 978-3-319-13278-5. The terminal half-life is about 38 h. A portion of the drug is metabolized by hydrolysis to cyproterone and acetic acid. However, in contrast to many other steroid esters hydrolysis is not extensive, and much of the pharmacological activity is exerted by the acetate form. Excretion is about 70% in the feces, mainly in the form of glucuronidated metabolites, and about 30% in the urine, predominantly as non-conjugated metabolites.
^ ^a ^b Barradell LB, Faulds D (July 1994). "Cyproterone. A review of its pharmacology and therapeutic efficacy in prostate cancer". Drugs Aging. 5 (1): 59–80. doi:10.2165/00002512-199405010-00006. PMID 7919640.
^ ^a ^b AAPL Newsletter (PDF). The Academy. 1998. Diarsipkan dari versi asli (PDF) tanggal 30 August 2017. Diakses tanggal 16 August 2016. CPA is 100% bioavailable when taken orally with a half life of 38 hours. The injectable form reaches maximum plasma levels in 82 hours and has a half life of about 72 hours.
^ Neumann F (1994). "The antiandrogen cyproterone acetate: discovery, chemistry, basic pharmacology, clinical use and tool in basic research". Exp. Clin. Endocrinol. 102 (1): 1–32. doi:10.1055/s-0029-1211261 . PMID 8005205.
^ Neumann F (January 1977). "Pharmacology and potential use of cyproterone acetate". Horm. Metab. Res. 9 (1): 1–13. doi:10.1055/s-0028-1093574. PMID 66176.
^ Neumann F, Töpert M (November 1986). "Pharmacology of antiandrogens". Journal of Steroid Biochemistry. 25 (5B): 885–95. doi:10.1016/0022-4731(86)90320-1. PMID 2949114.

Artikel bertopik biokimia ini adalah sebuah rintisan. Anda dapat membantu Wikipedia dengan mengembangkannya.

[pmid16112947-1] Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947.

[pmid2977383-2] Huber J, Zeillinger R, Schmidt J, Täuber U, Kuhnz W, Spona J (November 1988). "Pharmacokinetics of cyproterone acetate and its main metabolite 15 beta-hydroxy-cyproterone acetate in young healthy women". International Journal of Clinical Pharmacology, Therapy, and Toxicology. 26 (11): 555–561. PMID 2977383.

[pmid26327902-3] Bińkowska M, Woroń J (June 2015). "Progestogens in menopausal hormone therapy". Przeglad Menopauzalny = Menopause Review. 14 (2): 134–143. doi:10.5114/pm.2015.52154. PMC 4498031 . PMID 26327902.

[pmid14670641-4] Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH (December 2003). "Classification and pharmacology of progestins". Maturitas. 46 Suppl 1 (Suppl 1): S7–S16. doi:10.1016/j.maturitas.2003.09.014. PMID 14670641. Since there is no binding of CPA to SHBG and CBG in the serum, 93% of the compound is bound to serum albumin.

[Wakelin-2002-quote-1-5] Wakelin SH, Maibach HI, Archer CB (1 June 2002). Systemic Drug Treatment in Dermatology: A Handbook. CRC Press. hlm. 32–. ISBN 978-1-84076-013-2. Diarsipkan dari versi asli tanggal 14 January 2023. Diakses tanggal 27 September 2016. It is almost exclusively bound to plasma albumin.

[pmid6215538-6] Hammond GL, Lähteenmäki PL, Lähteenmäki P, Luukkainen T (October 1982). "Distribution and percentages of non-protein bound contraceptive steroids in human serum". Journal of Steroid Biochemistry. 17 (4): 375–380. doi:10.1016/0022-4731(82)90629-X. PMID 6215538.

[Dickman-2012-7] Dickman A (27 September 2012). Drugs in Palliative Care. OUP Oxford. hlm. 137–138. ISBN 978-0-19-966039-1.

[Boarder-2010-8] Boarder M, Newby D, Navti P (25 March 2010). Pharmacology for Pharmacy and the Health Sciences: A Patient-centred Approach. OUP Oxford. hlm. 632–. ISBN 978-0-19-955982-4. Diarsipkan dari versi asli tanggal 6 July 2024. Diakses tanggal 27 September 2016.

[Weber-2015-9] Weber GF (22 July 2015). Molecular Therapies of Cancer. Springer. hlm. 316–. ISBN 978-3-319-13278-5. The terminal half-life is about 38 h. A portion of the drug is metabolized by hydrolysis to cyproterone and acetic acid. However, in contrast to many other steroid esters hydrolysis is not extensive, and much of the pharmacological activity is exerted by the acetate form. Excretion is about 70% in the feces, mainly in the form of glucuronidated metabolites, and about 30% in the urine, predominantly as non-conjugated metabolites.

[pmid7919640-10] Barradell LB, Faulds D (July 1994). "Cyproterone. A review of its pharmacology and therapeutic efficacy in prostate cancer". Drugs Aging. 5 (1): 59–80. doi:10.2165/00002512-199405010-00006. PMID 7919640.

[BradfordKaye1998-11] AAPL Newsletter (PDF). The Academy. 1998. Diarsipkan dari versi asli (PDF) tanggal 30 August 2017. Diakses tanggal 16 August 2016. CPA is 100% bioavailable when taken orally with a half life of 38 hours. The injectable form reaches maximum plasma levels in 82 hours and has a half life of about 72 hours.

[pmid8005205-12] Neumann F (1994). "The antiandrogen cyproterone acetate: discovery, chemistry, basic pharmacology, clinical use and tool in basic research". Exp. Clin. Endocrinol. 102 (1): 1–32. doi:10.1055/s-0029-1211261 . PMID 8005205.

[pmid66176-13] Neumann F (January 1977). "Pharmacology and potential use of cyproterone acetate". Horm. Metab. Res. 9 (1): 1–13. doi:10.1055/s-0028-1093574. PMID 66176.

[pmid2949114-14] Neumann F, Töpert M (November 1986). "Pharmacology of antiandrogens". Journal of Steroid Biochemistry. 25 (5B): 885–95. doi:10.1016/0022-4731(86)90320-1. PMID 2949114.

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