維A酸

維A酸
臨床資料
商品名（英語：Drug nomenclature）	Avita, Renova, Retin-a
AHFS/Drugs.com	Monograph
MedlinePlus	a682437
核准狀況	美 DailyMed: 54982;
懷孕分級	澳: X (口服), D (局部) ; ;
給藥途徑	局部、口服
ATC碼	D10AD01 (WHO) L01XX14;
法律規範狀態
法律規範	澳：限醫生處方（S4）; 英：處方藥（℞-only） (POM); 美：處方藥（℞-only）;
藥物動力學數據
血漿蛋白結合率	> 95%
生物半衰期	0.5-2 小時
識別資訊
	IUPAC命名法 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl) -nona-2,4,6,8-tetraenoic acid ; 3,7-二甲基-9-（2,6,6-三甲基-1-環己烯）-反-2,4,6,8-壬四烯酸; ;
CAS號	302-79-4
PubChem CID	444795;
IUPHAR/BPS	2644;
DrugBank	DB00755 ;
ChemSpider	392618 ;
UNII	5688UTC01R;
KEGG	D00094 ;
ChEBI	CHEBI:15367 ;
ChEMBL	ChEMBL38 ;
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID7021239 ;
ECHA InfoCard	100.005.573
化學資訊
化學式	C20H28O2
摩爾質量	300.4412 g/mol
3D模型（JSmol（英語：JSmol））	交互式圖像;
熔點	180 °C（356 °F）
	SMILES O=C(O)\C=C(\C=C\C=C(\C=C\C1=C(\CCCC1(C)C)C)C)C;
	InChI InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+ ; Key:SHGAZHPCJJPHSC-YCNIQYBTSA-N ;

維A酸（Tretinoin、ATRA），又稱全反式維甲酸及視黃酸，分子式：C₂₀H₂₈O₂，分子量300.44，CAS號302-79-4，熔點180℃，是一種治療痤瘡和急性早幼粒細胞白血病的藥物^[5]^[6]^[7]。對於痤瘡，它以乳霜、凝膠、或軟膏的形式塗抹在皮膚上^[7]。對於白血病，口服長達三個月^[5]。局部維A酸也是最廣泛研究的用於光老化（英語：Photoaging）的類維生素A療法^[8]。

用作乳霜時的常見副作用僅限於皮膚，包括皮膚發紅、脫皮、和對日光敏感^[7]。口服時，副作用包括呼吸困難、頭痛、麻木、抑鬱、皮膚乾燥、瘙癢、脫髮、嘔吐、肌肉疼痛、和視力變化^[5]。其他嚴重的副作用包括高白細胞計數和血栓^[5]。由於存在出生缺陷的風險，妊娠期間禁止使用^[5]^[1]。它屬於類維生素A藥物家族^[6]。

維A酸於1957年獲得專利，並於1962年獲准用於醫療用途^[9]。它在世界衛生組織基本藥物標準清單清單中^[10]。維A酸可用作通用名藥物.^[11]。 2019年，它是美國第244種最常用的處方藥，處方量超過100萬張^[12]^[13]。

醫療用途

皮膚使用

維A酸最常用於治療痤瘡^[4]，包括炎症性和非炎症性。多項研究支持外用維A酸治療尋常痤瘡的療效^[14]^[15]。它有時與其他局部痤瘡藥物結合使用以增強其滲透性^[16]。除了治療活動性痤瘡外，維A酸還可加速痤瘡引起的炎症後色素沉著（英語：Hyperpigmentation）過度的消退^[17]。對於對初始治療有反應的人，它也可用作維持治療，減少長期使用抗生素治療痤瘡^[18]。

白血病

維A酸用於誘導急性早幼粒細胞白血病患者的緩解，這些患者有突變（t(15;17) 易位 160 和/或存在 PML/RARα 基因）並且對蒽環類藥物無反應或不能服用該類藥物。它不用於維持治療^[3]^[19]^[20]。

對於急性髓性白血病患者除了化療外，維A酸對腹瀉、噁心/嘔吐和心臟相關毒性 III/IV 級的影響的證據非常不確定。此外，除了化療之外，維A酸可能對死亡率、復發、進展、試驗期間的死亡率和感染等級 III/IV 幾乎沒有差異^[21]。

副作用

皮膚使用

外用維A酸僅用於皮膚，不應用於眼睛或粘膜組織。常見的副作用包括皮膚刺激、發紅、腫脹和起泡^[4]。

參見

參考文獻

^ ^1.0 ^1.1 Tretinoin (Vesanoid) Use During Pregnancy. Drugs.com. 25 July 2019 [16 January 2020]. （原始內容存檔於2019-08-21）.
^ Tretinoin topical Use During Pregnancy. Drugs.com. 1 July 2019 [16 January 2020]. （原始內容存檔於2020-11-29）.
^ ^3.0 ^3.1 Tretinoin capsule. DailyMed. 12 December 2018 [16 January 2020]. （原始內容存檔於2021-08-29）.
^ ^4.0 ^4.1 ^4.2 Tretinoin Cream- tretinoin cream. DailyMed. 1 December 2018 [16 January 2020]. （原始內容存檔於2021-04-11）.
^ ^5.0 ^5.1 ^5.2 ^5.3 ^5.4 Tretinoin. The American Society of Health-System Pharmacists. [8 December 2016]. （原始內容存檔於30 November 2016）.
^ ^6.0 ^6.1 Tivnan, Amanda. Resistance to Targeted Therapies Against Adult Brain Cancers. Springer. 2016: 123. ISBN 978-3-319-46505-0. （原始內容存檔於2017-11-05）.
^ ^7.0 ^7.1 ^7.2 British national formulary : BNF 69 69. British Medical Association. 2015: 627, 821–822. ISBN 978-0-85711-156-2.
^ Retinoids, topical. American Osteopathic College of Dermatology. [2022-08-15]. （原始內容存檔於2022-08-07）.
^ Fischer J, Ganellin CR. Analogue-based Drug Discovery. John Wiley & Sons. 2006: 476. ISBN 978-3-527-60749-5. （原始內容存檔於5 November 2017）.
^ World Health Organization. World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. 2019. hdl:10665/325771 . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
^ Tretinoin topical. The American Society of Health-System Pharmacists. [8 December 2016]. （原始內容存檔於16 May 2016）.
^ The Top 300 of 2019. ClinCalc. [16 October 2021]. （原始內容存檔於2021-02-12）.
^ Tretinoin – Drug Usage Statistics. ClinCalc. [16 October 2021]. （原始內容存檔於2020-07-08）.
^ Leyden JJ, Shalita A, Thiboutot D, Washenik K, Webster G. Topical retinoids in inflammatory acne: a retrospective, investigator-blinded, vehicle-controlled, photographic assessment. Clinical Therapeutics. February 2005, 27 (2): 216–24. PMID 15811485. doi:10.1016/j.clinthera.2005.02.009.
^ Webster G, Cargill DI, Quiring J, Vogelson CT, Slade HB. A combined analysis of 2 randomized clinical studies of tretinoin gel 0.05% for the treatment of acne. Cutis. March 2009, 83 (3): 146–54. PMID 19363908.
^ Gollnick H, Cunliffe W, Berson D, Dreno B, Finlay A, Leyden JJ, et al. Management of acne: a report from a Global Alliance to Improve Outcomes in Acne. Journal of the American Academy of Dermatology. July 2003, 49 (1 Suppl): S1–37. PMID 12833004. doi:10.1067/mjd.2003.618.
^ Kang S, Voorhees JJ. Topical retinoids. In: Fitzpatrick's Dermatology in General Medicine, 7th ed, Wolff K, Goldsmith LA, Katz SI, et al (Eds), McGraw Hill, New York 2008. p.2106.
^ Leyden, James; Stein-Gold, Linda; Weiss, Jonathan. Why Topical Retinoids Are Mainstay of Therapy for Acne. Dermatology and Therapy. 5 June 2017, 7 (3): 293–304. ISSN 2193-8210. PMC 5574737 . PMID 28585191. doi:10.1007/s13555-017-0185-2.
^ Huang ME, Ye YC, Chen SR, Chai JR, Lu JX, Zhoa L, et al. Use of all-trans retinoic acid in the treatment of acute promyelocytic leukemia (PDF). Blood. August 1988, 72 (2): 567–72. PMID 3165295. doi:10.1182/blood.V72.2.567.567 .
^ Castaigne S, Chomienne C, Daniel MT, Ballerini P, Berger R, Fenaux P, Degos L. All-trans retinoic acid as a differentiation therapy for acute promyelocytic leukemia. I. Clinical results (PDF). Blood. November 1990, 76 (9): 1704–9. PMID 2224119. doi:10.1182/blood.V76.9.1704.1704 .
^ Küley-Bagheri Y, Kreuzer KA, Monsef I, Lübbert M, Skoetz N. Cochrane Haematological Malignancies Group , 編. Effects of all-trans retinoic acid (ATRA) in addition to chemotherapy for adults with acute myeloid leukaemia (AML) (non-acute promyelocytic leukaemia (non-APL)). The Cochrane Database of Systematic Reviews. August 2018, 2018 (8): CD011960. PMC 6513628 . PMID 30080246. doi:10.1002/14651858.CD011960.pub2.

外部連結

Prescription Medications for Treating Acne. American Academy of Dermatology. （原始內容存檔於2012-06-20）.
Tretinoin AHFS Consumer Medication Information （頁面存檔備份，存於網際網路檔案館） at PubMed Health
Tretinoin Cream Prescribing Information （頁面存檔備份，存於網際網路檔案館） Drugs.com
Retin-A Cream, Gel, Liquid Prescribing Information （頁面存檔備份，存於網際網路檔案館） Drugs.com

[Drugs.com_oral_pregnancy-1] 1.0 ^1.1 Tretinoin (Vesanoid) Use During Pregnancy. Drugs.com. 25 July 2019 [16 January 2020]. （原始內容存檔於2019-08-21）.

[Drugs.com_topical_pregnancy-2] Tretinoin topical Use During Pregnancy. Drugs.com. 1 July 2019 [16 January 2020]. （原始內容存檔於2020-11-29）.

[OralLabel-3] 3.0 ^3.1 Tretinoin capsule. DailyMed. 12 December 2018 [16 January 2020]. （原始內容存檔於2021-08-29）.

[TopicalLabel-4] 4.0 ^4.1 ^4.2 Tretinoin Cream- tretinoin cream. DailyMed. 1 December 2018 [16 January 2020]. （原始內容存檔於2021-04-11）.

[AHFS2016-5] 5.0 ^5.1 ^5.2 ^5.3 ^5.4 Tretinoin. The American Society of Health-System Pharmacists. [8 December 2016]. （原始內容存檔於30 November 2016）.

[Tiv2016-6] 6.0 ^6.1 Tivnan, Amanda. Resistance to Targeted Therapies Against Adult Brain Cancers. Springer. 2016: 123. ISBN 978-3-319-46505-0. （原始內容存檔於2017-11-05）.

[BNF69-7] 7.0 ^7.1 ^7.2 British national formulary : BNF 69 69. British Medical Association. 2015: 627, 821–822. ISBN 978-0-85711-156-2.

[8] Retinoids, topical. American Osteopathic College of Dermatology. [2022-08-15]. （原始內容存檔於2022-08-07）.

[Fis2006-9] Fischer J, Ganellin CR. Analogue-based Drug Discovery. John Wiley & Sons. 2006: 476. ISBN 978-3-527-60749-5. （原始內容存檔於5 November 2017）.

[WHO21st-10] World Health Organization. World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. 2019. hdl:10665/325771 . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

[AHFS2016B-11] Tretinoin topical. The American Society of Health-System Pharmacists. [8 December 2016]. （原始內容存檔於16 May 2016）.

[12] The Top 300 of 2019. ClinCalc. [16 October 2021]. （原始內容存檔於2021-02-12）.

[13] Tretinoin – Drug Usage Statistics. ClinCalc. [16 October 2021]. （原始內容存檔於2020-07-08）.

[14] Leyden JJ, Shalita A, Thiboutot D, Washenik K, Webster G. Topical retinoids in inflammatory acne: a retrospective, investigator-blinded, vehicle-controlled, photographic assessment. Clinical Therapeutics. February 2005, 27 (2): 216–24. PMID 15811485. doi:10.1016/j.clinthera.2005.02.009.

[15] Webster G, Cargill DI, Quiring J, Vogelson CT, Slade HB. A combined analysis of 2 randomized clinical studies of tretinoin gel 0.05% for the treatment of acne. Cutis. March 2009, 83 (3): 146–54. PMID 19363908.

[pmid12833004-16] Gollnick H, Cunliffe W, Berson D, Dreno B, Finlay A, Leyden JJ, et al. Management of acne: a report from a Global Alliance to Improve Outcomes in Acne. Journal of the American Academy of Dermatology. July 2003, 49 (1 Suppl): S1–37. PMID 12833004. doi:10.1067/mjd.2003.618.

[Kang_S_2008-17] Kang S, Voorhees JJ. Topical retinoids. In: Fitzpatrick's Dermatology in General Medicine, 7th ed, Wolff K, Goldsmith LA, Katz SI, et al (Eds), McGraw Hill, New York 2008. p.2106.

[18] Leyden, James; Stein-Gold, Linda; Weiss, Jonathan. Why Topical Retinoids Are Mainstay of Therapy for Acne. Dermatology and Therapy. 5 June 2017, 7 (3): 293–304. ISSN 2193-8210. PMC 5574737 . PMID 28585191. doi:10.1007/s13555-017-0185-2.

[19] Huang ME, Ye YC, Chen SR, Chai JR, Lu JX, Zhoa L, et al. Use of all-trans retinoic acid in the treatment of acute promyelocytic leukemia (PDF). Blood. August 1988, 72 (2): 567–72. PMID 3165295. doi:10.1182/blood.V72.2.567.567 .

[20] Castaigne S, Chomienne C, Daniel MT, Ballerini P, Berger R, Fenaux P, Degos L. All-trans retinoic acid as a differentiation therapy for acute promyelocytic leukemia. I. Clinical results (PDF). Blood. November 1990, 76 (9): 1704–9. PMID 2224119. doi:10.1182/blood.V76.9.1704.1704 .

[21] Küley-Bagheri Y, Kreuzer KA, Monsef I, Lübbert M, Skoetz N. Cochrane Haematological Malignancies Group , 編. Effects of all-trans retinoic acid (ATRA) in addition to chemotherapy for adults with acute myeloid leukaemia (AML) (non-acute promyelocytic leukaemia (non-APL)). The Cochrane Database of Systematic Reviews. August 2018, 2018 (8): CD011960. PMC 6513628 . PMID 30080246. doi:10.1002/14651858.CD011960.pub2.

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