Details of the Drug

General Information of Drug (ID: DM27U4Y)

• Drug Name: Desogestrel
• Synonyms: Cerazette; Desogen; Desogestrelum; Organon Brand of Desogestrel; ORG 2969; Desogestrelum [INN-Latin]; Desogestrel (USAN/INN); Desogestrel [USAN:BAN:INN]; Alpha-pregn-4-en-20-yn-17-ol, 13-Ethyl-11-methylene-18,19-dinor-17; (17alpha)-13-Ethyl-11-methylene-18,19-dinorpregn-4-en-20-yn-17-ol; (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylidene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol; 13 Ethyl 11 methylene 18,19 dinor 17 alpha pregn 4 en 20 yn 17 ol; 13-Ethyl-11-methylene-18,19-dinor-17 alpha-pregn-4-en-20-yn-17-ol; 13-Ethyl-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-17-ol; 17alpha-ethynyl-11-methylidene-18a-homo-estr-4-en-17beta-ol

Indication

Disease Entry	ICD 11	Status	REF
Contraception	QA21	Approved	[1]

• Therapeutic Class: Contraceptive Agents
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 310.5
  Logarithm of the Partition Coefficient (xlogp); 4.9
  Rotatable Bond Count (rotbonds); 2
  Hydrogen Bond Donor Count (hbonddonor); 1
  Hydrogen Bond Acceptor Count (hbondacc); 1
• ADMET Property:
  Absorption AUC: The area under the plot of plasma concentration (AUC) of drug is 2000 mcgh/L [2]
  Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 48 mcg/L [2]
  Absorption Tmax: The time to maximum plasma concentration (Tmax) is 1.5 h [2]
  BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [3]
  Bioavailability: The bioavailability of drug is 39% [2]
  Clearance: The clearance of drug is 2 mL/min/kg []
  Elimination: The elimination of desogestrel is only done as the metabolites and not as the unchanged drug and about 85% of the administered dose can be excreted as metabolites after 6-8 days []
  Half-life: The concentration or amount of drug in body reduced by one-half in 30 hours []
  Metabolism: The drug is metabolized via the first-pass hepatic metabolism to form the major biologically active metabolite of desogestrel []
  MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.00805 micromolar/kg/day [4]
  Vd: The volume of distribution (Vd) of drug is 1.5 L/kg []
  Water Solubility: The ability of drug to dissolve in water is measured as 0.32 mg/mL [3]
• Chemical Identifiers:
  Formula: C22H30O
  IUPAC Name: (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylidene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
  Canonical SMILES: CC[C@]12CC(=C)[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CCCC[C@H]34
  InChI: InChI=1S/C22H30O/c1-4-21-14-15(3)20-17-9-7-6-8-16(17)10-11-18(20)19(21)12-13-22(21,23)5-2/h2,8,17-20,23H,3-4,6-7,9-14H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1
  InChIKey: RPLCPCMSCLEKRS-BPIQYHPVSA-N
• Cross-matching ID:
  PubChem CID: 40973
  ChEBI ID: CHEBI:4453
  CAS Number: 54024-22-5
  DrugBank ID: DB00304
  TTD ID: D06CGB
  INTEDE ID: DR0438

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Progesterone receptor (PGR)	TTUV8G9	PRGR_HUMAN	Modulator	[5]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)	DE4LYSA	CP3A4_HUMAN	Substrate	[6]
Cytochrome P450 2C9 (CYP2C9)	DE5IED8	CP2C9_HUMAN	Substrate	[7]
Mephenytoin 4-hydroxylase (CYP2C19)	DEGTFWK	CP2CJ_HUMAN	Substrate	[7]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Aldo-keto reductase family 1 member C3 (AKR1C3)	OTU2SXBA	AK1C3_HUMAN	Gene/Protein Processing	[8]
Carboxypeptidase B2 (CPB2)	OTPIL8IE	CBPB2_HUMAN	Gene/Protein Processing	[9]
Cytochrome P450 1A2 (CYP1A2)	OTLLBX48	CP1A2_HUMAN	Gene/Protein Processing	[10]
Low-density lipoprotein receptor (LDLR)	OTH559LU	LDLR_HUMAN	Gene/Protein Processing	[11]
Vitamin K-dependent protein C (PROC)	OTGVH484	PROC_HUMAN	Gene/Protein Processing	[9]
Vitamin K-dependent protein S (PROS1)	OTXQWNOI	PROS_HUMAN	Gene/Protein Processing	[12]

Molecular Expression Atlas of This Drug

• The Studied Disease: Contraception
• ICD Disease Classification: QA21

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Progesterone receptor (PGR)	DTT	PGR	3.26E-38	-3.79	-2.5
Mephenytoin 4-hydroxylase (CYP2C19)	DME	CYP2C19	1.07E-03	-2.00E-01	-3.54E-01
Cytochrome P450 2C9 (CYP2C9)	DME	CYP2C9	4.46E-05	-2.53E-01	-2.36E-01
Cytochrome P450 3A4 (CYP3A4)	DME	CYP3A4	2.20E-02	-1.08E-01	-2.31E-01

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Desogestrel (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Metreleptin	DM1NOEK	Moderate	Decreased metabolism of Desogestrel caused by Metreleptin mediated inhibition of CYP450 enzyme.	Acute diabete complication [5A2Y]	[13]
Siltuximab	DMGEATB	Moderate	Altered metabolism of Desogestrel due to Siltuximab alters the formation of CYP450 enzymes.	Anemia [3A00-3A9Z]	[14]
Clobazam - Lundbeck	DMW1OQ0	Moderate	Increased metabolism of Desogestrel caused by Clobazam - Lundbeck mediated induction of CYP450 enzyme.	Anxiety disorder [6B00-6B0Z]	[15]
Voriconazole	DMAOL2S	Moderate	Decreased metabolism of Desogestrel caused by Voriconazole mediated inhibition of CYP450 enzyme.	Aspergillosis [1F20]	[16]
Posaconazole	DMUL5EW	Moderate	Decreased metabolism of Desogestrel caused by Posaconazole mediated inhibition of CYP450 enzyme.	Aspergillosis [1F20]	[16]
Telithromycin	DMZ4P3A	Moderate	Decreased metabolism of Desogestrel caused by Telithromycin mediated inhibition of CYP450 enzyme.	Bacterial infection [1A00-1C4Z]	[17]
Lapatinib	DM3BH1Y	Moderate	Decreased metabolism of Desogestrel caused by Lapatinib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[18]
Atorvastatin	DMF28YC	Minor	Decreased metabolism of Desogestrel caused by Atorvastatin mediated inhibition of CYP450 enzyme.	Cardiovascular disease [BA00-BE2Z]	[19]
Ivacaftor	DMZC1HS	Moderate	Decreased metabolism of Desogestrel caused by Ivacaftor mediated inhibition of CYP450 enzyme.	Cystic fibrosis [CA25]	[20]
MK-8228	DMOB58Q	Moderate	Decreased metabolism of Desogestrel caused by MK-8228 mediated inhibition of CYP450 enzyme.	Cytomegaloviral disease [1D82]	[21]
Aprepitant	DM053KT	Moderate	Increased metabolism of Desogestrel caused by Aprepitant mediated induction of CYP450 enzyme.	Depression [6A70-6A7Z]	[15]
Nefazodone	DM4ZS8M	Moderate	Decreased metabolism of Desogestrel caused by Nefazodone mediated inhibition of CYP450 enzyme.	Depression [6A70-6A7Z]	[18]
Oxcarbazepine	DM5PU6O	Major	Increased metabolism of Desogestrel caused by Oxcarbazepine mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[22]
Rufinamide	DMWE60C	Moderate	Increased metabolism of Desogestrel caused by Rufinamide mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[23]
Telaprevir	DMMRV29	Major	Increased metabolism of Desogestrel caused by Telaprevir mediated induction of CYP450 enzyme.	Hepatitis virus infection [1E50-1E51]	[15]
Rifapentine	DMCHV4I	Major	Increased metabolism of Desogestrel caused by Rifapentine mediated induction of CYP450 enzyme.	HIV-infected patients with tuberculosis [1B10-1B14]	[24]
Efavirenz	DMC0GSJ	Moderate	Increased metabolism of Desogestrel caused by Efavirenz mediated induction of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[15]
Saquinavir	DMG814N	Moderate	Decreased metabolism of Desogestrel caused by Saquinavir mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[21]
Darunavir	DMN3GCH	Moderate	Decreased metabolism of Desogestrel caused by Darunavir mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[25]
BMS-201038	DMQTAGO	Moderate	Decreased metabolism of Desogestrel caused by BMS-201038 mediated inhibition of CYP450 enzyme.	Hyper-lipoproteinaemia [5C80]	[26]
Miltefosine	DMND304	Moderate	Altered absorption of Desogestrel caused by Miltefosine.	Leishmaniasis [1F54]	[13]
Glycerol phenylbutyrate	DMDGRQO	Moderate	Increased metabolism of Desogestrel caused by Glycerol phenylbutyrate mediated induction of CYP450 enzyme.	Liver disease [DB90-DB9Z]	[23]
Vemurafenib	DM62UG5	Moderate	Increased metabolism of Desogestrel caused by Vemurafenib mediated induction of CYP450 enzyme.	Melanoma [2C30]	[27]
Dabrafenib	DMX6OE3	Major	Increased metabolism of Desogestrel caused by Dabrafenib mediated induction of CYP450 enzyme.	Melanoma [2C30]	[15]
Exjade	DMHPRWG	Moderate	Increased metabolism of Desogestrel caused by Exjade mediated induction of CYP450 enzyme.	Mineral absorption/transport disorder [5C64]	[26]
Bexarotene	DMOBIKY	Major	Increased metabolism of Desogestrel caused by Bexarotene mediated induction of CYP450 enzyme.	Mycosis fungoides [2B01]	[15]
E-2007	DMJDYNQ	Moderate	Increased metabolism of Desogestrel caused by E-2007 mediated induction of CYP450 enzyme.	Neuropathy [8C0Z]	[23]
Tocilizumab	DM7J6OR	Moderate	Altered metabolism of Desogestrel due to Tocilizumab alters the formation of CYP450 enzymes.	Rheumatoid arthritis [FA20]	[14]
Rilonacept	DMGLUQS	Moderate	Altered metabolism of Desogestrel due to Rilonacept alters the formation of CYP450 enzymes.	Rheumatoid arthritis [FA20]	[14]
Sarilumab	DMOGNXY	Moderate	Altered metabolism of Desogestrel due to Sarilumab alters the formation of CYP450 enzymes.	Rheumatoid arthritis [FA20]	[14]
Voxelotor	DMCS6M5	Moderate	Decreased metabolism of Desogestrel caused by Voxelotor mediated inhibition of CYP450 enzyme.	Sickle-cell disorder [3A51]	[13]
Telotristat ethyl	DMDIYFZ	Moderate	Increased metabolism of Desogestrel caused by Telotristat ethyl mediated induction of CYP450 enzyme.	Small intestine developmental anomaly [DA90]	[23]
Pitolisant	DM8RFNJ	Moderate	Increased metabolism of Desogestrel caused by Pitolisant mediated induction of CYP450 enzyme.	Somnolence [MG42]	[23]
Tizanidine	DMR2IQ4	Major	Decreased metabolism of Desogestrel caused by Tizanidine mediated inhibition of CYP450 enzyme.	Tonus and reflex abnormality [MB47]	[28]

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