醋酸甲羥孕酮

醋酸甲羥孕酮
臨床資料
讀音	/mɛˌdrɒksiproʊˈdʒɛstəroʊn ˈæsɪteɪt/ me-DROKS-ee-proh-JES-tər-ohn ASS-i-tayt
商品名（英語：Drug nomenclature）	Depo-Provera, others
其他名稱	MPA; DMPA; Methylhydroxyprogesterone acetate; Methylacetoxyprogesterone; MAP; Methypregnone; Metipregnone; 6α-Methyl-17α-hydroxyprogesterone acetate; 6α-Methyl-17α-acetoxyprogesterone; 6α-Methyl-17α-hydroxypregn-4-ene-3,20-dione acetate; NSC-26386
AHFS/Drugs.com	Monograph
MedlinePlus	a604039
懷孕分級	澳: D ; ;
給藥途徑	口服給藥、舌下、肌肉注射、皮下注射
藥物類別（英語：Drug class）	黃體酯酮 (藥物)（英語：Progestogen (medication)）；黃體素；孕激素酯（英語：Progestogen ester）；抗促性腺激素（英語：Antigonadotropin）；類固醇類抗雄激素（英語：Steroidal antiandrogen）
ATC碼	G03AC06 (WHO) G03DA02, L02AB02;
法律規範狀態
法律規範	澳：限醫生處方（S4）; 加：處方藥（℞-only）; 美：處方藥（℞-only）; 處方藥（℞-only）;
藥物動力學數據
生物利用度	口服：~100%
血漿蛋白結合率	88%（血清白蛋白）
藥物代謝	肝臟（羥基化 (CYP3A4)，氧化還原反應，conjugation（英語：conjugation (biochemistry)）)
生物半衰期	口服：12–33小時; IM (aq. susp.): ~50 days; SC (aq. susp.): ~40 days
排泄途徑	尿 (as conjugate（英語：conjugation (biochemistry)）s)
識別資訊
	IUPAC命名法 [(6S,8R,9S,10R,13S,14S,17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate; ;
CAS號	71-58-9
PubChem CID	6279;
IUPHAR/BPS	2879;
DrugBank	DB00603;
ChemSpider	6043;
UNII	C2QI4IOI2G;
KEGG	C08150 ;
ChEBI	CHEBI:6716;
ChEMBL	ChEMBL717 ;
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID0025527 ;
ECHA InfoCard	100.000.689
化學資訊
化學式	C24H34O4
摩爾質量	386.53 g·mol−1
3D模型（JSmol（英語：JSmol））	交互式圖像;
熔點	207至209 °C（405至408 °F）
	SMILES C[C@H]1C[C@@H]2[C@H](CC[C@]3([C@H]2CC[C@@]3(C(=O)C)OC(=O)C)C)[C@@]4(C1=CC(=O)CC4)C;
	InChI InChI=InChI=1S/C24H34O4/c1-14-12-18-19(22(4)9-6-17(27)13-21(14)22)7-10-23(5)20(18)8-11-24(23,15(2)25)28-16(3)26/h13-14,18-20H,6-12H2,1-5H3/t14-,18+,19-,20-,22+,23-,24-/m0/s1; Key:PSGAAPLEWMOORI-PEINSRQWSA-N;

醋酸甲羥孕酮（Medroxyprogesterone acetate，MPA），其中注射劑型的醋酸甲羥孕酮（depot medroxyprogesterone acetate，DMPA），商品名包括狄波-普維拉（Depo-Provera），是黃體酯酮 (藥物)（英語：Progestogen (medication)）類激素藥物^[8] ^[3]。適應範圍，包括避孕與激素替代療法^[8] ^[3]。也可用於治療子宮內膜異位症、異常子宮出血、男性的性別認知異常及某些類型的癌症^[8]。藥物可單獨使用，也可與雌激素(藥物)（英語：Estrogen (medication)）併用^[9] ^[10]。有口服、舌下、肌肉或皮下注射等不同劑型^[8]。

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常見的副作用包括月經失調（如閉經）、腹痛和頭痛^[8]。更嚴重的副作用包括骨質流失、血栓、過敏和肝臟問題^[8]。不建議在懷孕期使用，因可能傷害嬰兒^[8]。醋酸甲羥孕酮是一種人工合成的黃體酯酮 (藥物)（英語：Progestogen (medication)），它能活化孕酮受體，即孕酮的生物學靶點^[3]。它也具弱的糖皮質激素活性和非常弱的雄激素活性，但無其他重要的激素活性^[3] ^[11]。因為它的孕激素活性，使用後會減少人體的促性腺激素釋放，並抑制性激素濃度^[12]。它能抑制排卵而避孕^[8]。

醋酸甲羥孕酮在1956年被發現，在1959年取得美國的醫療使用許可^[13] ^[14] ^[8]。名列世界衛生組織基本藥物清單^[15]。它是停經後激素治療和純孕激素避孕藥中最常用的孕激素^[16] ^[17]。注射型藥物已在100多個國家取得長效型避孕藥的使用許可^[18] ^[19]。 2017年，它是美國最常用處方藥的第222名，處方數量超過200萬張^[20] ^[21]。

參見

結合型雌性激素/醋酸甲羥孕酮（英語：Conjugated estrogens/medroxyprogesterone acetate）
雌二醇/醋酸甲羥孕酮（英語：Estradiol/medroxyprogesterone acetate）
環戊丙酸雌二醇/醋酸甲羥孕酮
聚磷酸雌二醇/醋酸甲羥孕酮（英語：Polyestradiol phosphate/medroxyprogesterone acetate）

參考文獻

[1]
Medroxyprogesterone Uses, Dosage & Side Effects.
[2]
Product monograph brand safety updates. Health Canada. February 2024 [24 March 2024].
[3]
Kuhl H. Pharmacology of estrogens and progestogens: influence of different routes of administration (PDF). Climacteric. 2005, 8 (Suppl 1): 3–63. PMID 16112947. S2CID 24616324. doi:10.1080/13697130500148875.
[4]
Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH. Classification and pharmacology of progestins. Maturitas. 2008, 61 (1–2): 171–80. PMID 19434889. doi:10.1016/j.maturitas.2008.11.013.
[5]
Provera (PDF). FDA. 2015 [31 March 2018]. （原始內容 (PDF)存檔於11 February 2017）.
[6]
Depo_Provera (PDF). FDA. 2016 [31 March 2018].
[7]
depo-subQ Provera (PDF). FDA. 2017 [31 March 2018].
[8]
Medroxyprogesterone Acetate. The American Society of Health-System Pharmacists. [8 December 2016]. （原始內容存檔於24 December 2016）.
[9]
Archive copy. [2017-11-24]. （原始內容存檔於2018-08-03）.
[10]
Sweetman, Sean C. (編). https://web.archive.org/web/20210828162143/https://about.medicinescomplete.com/wp-content/plugins/revslider/public/assets/js/extensions/revolution.extension.parallax.min.js?version=5.4.5 |archiveurl=缺少標題 (幫助). Martindale: The Complete Drug Reference 36th. London: Pharmaceutical Press. 2009: 2113–2114 [2018-04-01]. ISBN 978-0-85369-840-1. （原始內容存檔於2021-08-28）.
[11]
Kemppainen JA, Langley E, Wong CI, Bobseine K, Kelce WR, Wilson EM. Distinguishing androgen receptor agonists and antagonists: distinct mechanisms of activation by medroxyprogesterone acetate and dihydrotestosterone. Molecular Endocrinology. March 1999, 13 (3): 440–54. PMID 10077001. doi:10.1210/mend.13.3.0255.
[12]
Genazzani AR. Frontiers in Gynecologic and Obstetric Investigation. Taylor & Francis. 15 January 1993: 320. ISBN 978-1-85070-486-7. （原始內容存檔於20 May 2016）.
[13]
Stanley M. Roberts. Introduction to Biological and Small Molecule Drug Research and Development: Chapter 12. Hormone replacement therapy. Elsevier Science. 7 May 2013: 9– [3 April 2018]. ISBN 978-0-12-806202-9. （原始內容存檔於1 August 2020）. [...] medroxyprogesterone acetate, also known as Provera^® (discovered simultaneously by Searle and Upjohn in 1956) [..]
[14]
Sneader, Walter. Chapter 18: Hormone analogs. New York: Wiley. 2005: 204. ISBN 0-471-89980-1.
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World Health Organization. World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. 2019. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
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A. Wayne Meikle. Hormone Replacement Therapy. Springer Science & Business Media. 1 June 1999: 383– [20 July 2018]. ISBN 978-1-59259-700-0. （原始內容存檔於1 August 2020）.
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Special Programme of Research, Development, and Research Training in Human Reproduction (World Health Organization); World Health Organization. Research on Reproductive Health at WHO: Biennial Report 2000-2001. World Health Organization. 2002: 17– [2018-07-20]. ISBN 978-92-4-156208-9. （原始內容存檔於2020-08-01）.
[18]
Bagade O, Pawar V, Patel R, Patel B, Awasarkar V, Diwate S. Increasing use of long-acting reversible contraception: safe, reliable, and cost-effective birth control (PDF). World J Pharm Pharm Sci. 2014, 3 (10): 364–392 [2018-08-02]. ISSN 2278-4357. （原始內容 (PDF)存檔於2017-08-10）.
[19]
Sulochana Gunasheela. Practical Management of Gynecological Problems. JP Medical Ltd. 14 March 2011: 39– [2 August 2018]. ISBN 978-93-5025-240-6. （原始內容存檔於1 August 2020）.
[20]
The Top 300 of 2020. ClinCalc. [11 April 2020]. （原始內容存檔於12 February 2021）.
[21]
Medroxyprogesterone Acetate - Drug Usage Statistics. ClinCalc. [11 April 2020]. （原始內容存檔於2 July 2020）.

[Drugs.com-2-1] [1]
Medroxyprogesterone Uses, Dosage & Side Effects.

[2] [2]
Product monograph brand safety updates. Health Canada. February 2024 [24 March 2024].

[pmid16112947-3] [3]
Kuhl H. Pharmacology of estrogens and progestogens: influence of different routes of administration (PDF). Climacteric. 2005, 8 (Suppl 1): 3–63. PMID 16112947. S2CID 24616324. doi:10.1080/13697130500148875.

[pmid19434889-4] [4]
Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH. Classification and pharmacology of progestins. Maturitas. 2008, 61 (1–2): 171–80. PMID 19434889. doi:10.1016/j.maturitas.2008.11.013.

[ProveraLabel-5] [5]
Provera (PDF). FDA. 2015 [31 March 2018]. （原始內容 (PDF)存檔於11 February 2017）.

[DepoProveraLabel-6] [6]
Depo_Provera (PDF). FDA. 2016 [31 March 2018].

[DepoSubQProveraLabel-7] [7]
depo-subQ Provera (PDF). FDA. 2017 [31 March 2018].

[AHFS2016-8] [8]
Medroxyprogesterone Acetate. The American Society of Health-System Pharmacists. [8 December 2016]. （原始內容存檔於24 December 2016）.

[Drugs.com-9] [9]
Archive copy. [2017-11-24]. （原始內容存檔於2018-08-03）.

[Martindale-10] [10]
Sweetman, Sean C. (編). https://web.archive.org/web/20210828162143/https://about.medicinescomplete.com/wp-content/plugins/revslider/public/assets/js/extensions/revolution.extension.parallax.min.js?version=5.4.5 |archiveurl=缺少標題 (幫助). Martindale: The Complete Drug Reference 36th. London: Pharmaceutical Press. 2009: 2113–2114 [2018-04-01]. ISBN 978-0-85369-840-1. （原始內容存檔於2021-08-28）.

[pmid10077001-11] [11]
Kemppainen JA, Langley E, Wong CI, Bobseine K, Kelce WR, Wilson EM. Distinguishing androgen receptor agonists and antagonists: distinct mechanisms of activation by medroxyprogesterone acetate and dihydrotestosterone. Molecular Endocrinology. March 1999, 13 (3): 440–54. PMID 10077001. doi:10.1210/mend.13.3.0255.

[Genazzani1993-12] [12]
Genazzani AR. Frontiers in Gynecologic and Obstetric Investigation. Taylor & Francis. 15 January 1993: 320. ISBN 978-1-85070-486-7. （原始內容存檔於20 May 2016）.

[Roberts2013-13] [13]
Stanley M. Roberts. Introduction to Biological and Small Molecule Drug Research and Development: Chapter 12. Hormone replacement therapy. Elsevier Science. 7 May 2013: 9– [3 April 2018]. ISBN 978-0-12-806202-9. （原始內容存檔於1 August 2020）. [...] medroxyprogesterone acetate, also known as Provera^® (discovered simultaneously by Searle and Upjohn in 1956) [..]

[Sneader2005-14] [14]
Sneader, Walter. Chapter 18: Hormone analogs. New York: Wiley. 2005: 204. ISBN 0-471-89980-1.

[WHO21st-15] [15]
World Health Organization. World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. 2019. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

[Meikle1999-16] [16]
A. Wayne Meikle. Hormone Replacement Therapy. Springer Science & Business Media. 1 June 1999: 383– [20 July 2018]. ISBN 978-1-59259-700-0. （原始內容存檔於1 August 2020）.

[Organization)Organization2002-17] [17]
Special Programme of Research, Development, and Research Training in Human Reproduction (World Health Organization); World Health Organization. Research on Reproductive Health at WHO: Biennial Report 2000-2001. World Health Organization. 2002: 17– [2018-07-20]. ISBN 978-92-4-156208-9. （原始內容存檔於2020-08-01）.

[BagadePawar2014-18] [18]
Bagade O, Pawar V, Patel R, Patel B, Awasarkar V, Diwate S. Increasing use of long-acting reversible contraception: safe, reliable, and cost-effective birth control (PDF). World J Pharm Pharm Sci. 2014, 3 (10): 364–392 [2018-08-02]. ISSN 2278-4357. （原始內容 (PDF)存檔於2017-08-10）.

[Gunasheela2011-19] [19]
Sulochana Gunasheela. Practical Management of Gynecological Problems. JP Medical Ltd. 14 March 2011: 39– [2 August 2018]. ISBN 978-93-5025-240-6. （原始內容存檔於1 August 2020）.

[ref-20] [20]
The Top 300 of 2020. ClinCalc. [11 April 2020]. （原始內容存檔於12 February 2021）.

[ref1-21] [21]
Medroxyprogesterone Acetate - Drug Usage Statistics. ClinCalc. [11 April 2020]. （原始內容存檔於2 July 2020）.

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