Details of the Drug-Related molecule(s) Interaction Atlas

General Information of Drug (ID: DMYP4XC)

Drug Name
Norgestimate Drug Info
Synonyms
Norgestimato; Norgestimatum; Dexnorgestrel acetime; Norgestrel oxime acetate; D 138; ORF 10131; RWJ 10131; Norgestimato [INN-Spanish]; Norgestimatum [INN-Latin]; ORF-10131; Ortho-Prefest; RWJ-10131; Norgestimate (USP/INN); Norgestimate [USAN:INN:BAN]; D-13beta-Ethyl-17alpha-ethynyl-17beta-acetoxygon-4-en-3-oneoxime; D-13-beta-Ethyl-17-alpha-ethynyl-17-beta-acetoxygon-4-en-3-one oxime; [(3E,8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate; (+)-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one oxime acetate (ester); (17-alpha)-17-(Acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-oxime; (17alpha)-17-(Acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-oxime; (3E)-17alpha-ethynyl-3-(hydroxyimino)-18a-homoestr-4-en-17beta-yl acetate
Indication
Disease Entry ICD 11 Status REF
Acne vulgaris ED80 Approved [1]
Contraception QA21 Approved [2]
Hot flushes GA30 Approved [1]
Obsolete atrophic vulva Approved [1]
Therapeutic Class
Contraceptive Agents
Cross-matching ID
PubChem CID
6540478
ChEBI ID
CHEBI:50815
CAS Number
CAS 20799-27-3
TTD Drug ID
DMYP4XC
INTEDE Drug ID
DR1178

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DME
DOT
Drug Status:
Approved Drug(s)
Download the Complete Related Drug List
Drug(s) Targeting Progesterone receptor (PGR)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Progesterone DMUY35B Amenorrhea GA20.0 Approved [7]
Desogestrel DM27U4Y Contraception QA21 Approved [8]
Ulipristal DMBNI20 Contraception QA21 Approved [9]
Etonogestrel DMKA8J4 Contraception QA21 Approved [3]
Megestrol DMDH9KX Breast cancer 2C60-2C65 Approved [10]
Segesterone acetate; ethinyl estradiol DMFEGB0 Contraception QA21 Approved [11]
Dydrogesterone DMAKIDV Menstrual disorder GA20.3 Approved [12]
Medroxyprogesterone DMBGWPH Solid tumour/cancer 2A00-2F9Z Approved [12]
Ethynodiol Diacetate DMZM84R Contraception QA21 Approved [13]
Levonorgestrel DM1DP7T Atypical endometrial hyperplasia Approved [14]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 3A4 (CYP3A4)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [15]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [16]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [17]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [18]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [19]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [20]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [21]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [22]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [16]
Verapamil DMA7PEW Angina pectoris BA40 Approved [23]
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Drug(s) Affected By ATP-binding cassette sub-family C member 2 (ABCC2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Lopinavir DMITQS0 Human immunodeficiency virus infection 1C62 Approved [24]
Sulfinpyrazone DMEV954 Gout FA25 Approved [25]
Probenecid DMMFWOJ Acute gonococcal cervicitis Approved [26]
Docetaxel DMDI269 Advanced cancer 2A00-2F9Z Approved [27]
Methotrexate DM2TEOL Anterior urethra cancer Approved [28]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [29]
Cholic Acid DM7OKQV Cholelithiasis DC11 Approved [30]
Epirubicin DMPDW6T Solid tumour/cancer 2A00-2F9Z Approved [31]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [32]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [33]
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Drug(s) Affected By Androgen receptor (AR)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [34]
Nilutamide DMFN07X Prostate cancer 2C82.0 Approved [34]
Hydroxyflutamide DMGIZF5 Prostate cancer 2C82.0 Approved [34]
Enzalutamide DMGL19D Prostate cancer 2C82.0 Approved [35]
Bicalutamide DMZMSPF Prostate cancer 2C82.0 Approved [36]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [37]
Drospirenone DM1A9W3 Acne vulgaris ED80 Approved [38]
Nitrendipine DM21C09 Hypertension BA00-BA04 Approved [39]
Selenium DM25CGV N. A. N. A. Approved [40]
Spironolactone DM2AQ5N Chronic heart failure BD1Z Approved [41]
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Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas
Download the Complete Interaction Atlas for Visualization in Cytoscape

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Progesterone receptor (PGR) TTUV8G9 PRGR_HUMAN Agonist [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) Main DME DE4LYSA CP3A4_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Androgen receptor (AR) OTUBKAZZ ANDR_HUMAN Gene/Protein Processing [5]
ATP-binding cassette sub-family C member 2 (ABCC2) OTJSIGV5 MRP2_HUMAN Gene/Protein Processing [6]

References

1 Norgestimate FDA Label
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3 Pharmacological profile of progestins. Maturitas. 2008 Sep-Oct;61(1-2):151-7.
4 Metabolite identification, reaction phenotyping, and retrospective drug-drug interaction predictions of 17-deacetylnorgestimate, the active component of the oral contraceptive norgestimate. Drug Metab Dispos. 2017 Jun;45(6):676-685.
5 Antiandrogenic activity of norgestimate in a human androgen-dependent stable-transfected cell line. Gynecol Endocrinol. 2007 Apr;23(4):193-7. doi: 10.1080/09513590701214414.
6 Interaction of progestins with the human multidrug resistance-associated protein 2 (MRP2). Drug Metab Dispos. 2005 Nov;33(11):1576-9.
7 Clinical pipeline report, company report or official report of lipocine.
8 Preclinical experience with two selective progesterone receptor modulators on breast and endometrium. Steroids. 2000 Oct-Nov;65(10-11):733-40.
9 Mullard A: 2010 FDA drug approvals. Nat Rev Drug Discov. 2011 Feb;10(2):82-5.
10 Focus on anastrozole and breast cancer. Curr Med Res Opin. 2003;19(8):683-8.
11 2018 FDA drug approvals.Nat Rev Drug Discov. 2019 Feb;18(2):85-89.
12 Dienogest is a selective progesterone receptor agonist in transactivation analysis with potent oral endometrial activity due to its efficient pharm... Steroids. 2008 Feb;73(2):222-31.
13 Contribution of functional groups of 19-nor-progestogens to binding to progesterone and estradiol-17beta receptors in rabbit uterus. Endocrinology. 1977 Jun;100(6):1579-84.
14 Met909 plays a key role in the activation of the progesterone receptor and also in the high potency of 13-ethyl progestins. Mol Pharmacol. 2009 Jun;75(6):1317-24.
15 Expression levels and activation of a PXR variant are directly related to drug resistance in osteosarcoma cell lines. Cancer. 2007 Mar 1;109(5):957-65.
16 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
17 Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75.
18 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
19 Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772.
20 Potent mechanism-based inhibition of CYP3A4 by imatinib explains its liability to interact with CYP3A4 substrates. Br J Pharmacol. 2012 Apr;165(8):2787-98.
21 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
22 The metabolism of zidovudine by human liver microsomes in vitro: formation of 3'-amino-3'-deoxythymidine. Biochem Pharmacol. 1994 Jul 19;48(2):267-76.
23 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
24 Functional defect caused by the 4544G>A SNP in ABCC2: potential impact for drug cellular disposition. Pharmacogenet Genomics. 2011 Dec;21(12):884-93. doi: 10.1097/FPC.0b013e32834d672b.
25 Role of multidrug resistance protein 2 (MRP2, ABCC2) in alkylating agent detoxification: MRP2 potentiates glutathione S-transferase A1-1-mediated resistance to chlorambucil cytotoxicity. J Pharmacol Exp Ther. 2004 Jan;308(1):260-7. doi: 10.1124/jpet.103.057729. Epub 2003 Oct 20.
26 MRP2 (ABCC2) transports taxanes and confers paclitaxel resistance and both processes are stimulated by probenecid. Int J Cancer. 2005 Sep 20;116(5):824-9. doi: 10.1002/ijc.21013.
27 Association of genetic polymorphisms in SLCO1B3 and ABCC2 with docetaxel-induced leukopenia. Cancer Sci. 2008 May;99(5):967-72.
28 Methotrexate normalizes up-regulated folate pathway genes in rheumatoid arthritis. Arthritis Rheum. 2013 Nov;65(11):2791-802.
29 In vitro study of transporters involved in intestinal absorption of inorganic arsenic. Chem Res Toxicol. 2012 Feb 20;25(2):446-53. doi: 10.1021/tx200491f. Epub 2012 Jan 26.
30 Potency of individual bile acids to regulate bile acid synthesis and transport genes in primary human hepatocyte cultures. Toxicol Sci. 2014 Oct;141(2):538-46. doi: 10.1093/toxsci/kfu151. Epub 2014 Jul 23.
31 Co-encapsulation of chrysophsin-1 and epirubicin in PEGylated liposomes circumvents multidrug resistance in HeLa cells. Chem Biol Interact. 2015 Dec 5;242:13-23. doi: 10.1016/j.cbi.2015.08.023. Epub 2015 Sep 1.
32 Evaluation of drug transporters' significance for multidrug resistance in head and neck squamous cell carcinoma. Head Neck. 2011 Jul;33(7):959-68. doi: 10.1002/hed.21559. Epub 2010 Aug 24.
33 Gene expression analysis of precision-cut human liver slices indicates stable expression of ADME-Tox related genes. Toxicol Appl Pharmacol. 2011 May 15;253(1):57-69.
34 TBECH, 1,2-dibromo-4-(1,2 dibromoethyl) cyclohexane, alters androgen receptor regulation in response to mutations associated with prostate cancer. Toxicol Appl Pharmacol. 2016 Sep 15;307:91-101. doi: 10.1016/j.taap.2016.07.018. Epub 2016 Jul 27.
35 Targeting chromatin binding regulation of constitutively active AR variants to overcome prostate cancer resistance to endocrine-based therapies. Nucleic Acids Res. 2015 Jul 13;43(12):5880-97. doi: 10.1093/nar/gkv262. Epub 2015 Apr 23.
36 Possible role of adaptive mutation in resistance to antiandrogen in prostate cancer cells. Prostate. 2005 Nov 1;65(3):268-75. doi: 10.1002/pros.20282.
37 Effects of the environmental estrogens bisphenol A, o,p'-DDT, p-tert-octylphenol and coumestrol on apoptosis induction, cell proliferation and the expression of estrogen sensitive molecular parameters in the human breast cancer cell line MCF-7. J Steroid Biochem Mol Biol. 2002 Jan;80(1):61-70. doi: 10.1016/s0960-0760(01)00173-x.
38 Identifying environmental chemicals as agonists of the androgen receptor by using a quantitative high-throughput screening platform. Toxicology. 2017 Jun 15;385:48-58. doi: 10.1016/j.tox.2017.05.001. Epub 2017 May 4.
39 Quantitative high-throughput profiling of environmental chemicals and drugs that modulate farnesoid X receptor. Sci Rep. 2014 Sep 26;4:6437. doi: 10.1038/srep06437.
40 Prostate specific antigen expression is down-regulated by selenium through disruption of androgen receptor signaling. Cancer Res. 2004 Jan 1;64(1):19-22. doi: 10.1158/0008-5472.can-03-2789.
41 Comparison of the Hershberger assay and androgen receptor binding assay of twelve chemicals. Toxicology. 2004 Feb 15;195(2-3):177-86. doi: 10.1016/j.tox.2003.09.012.