Details of the Drug

General Information of Drug (ID: DMU9MYJ)

Drug Name

Oxandrolone

Synonyms

Anavar; Lonavar; Ossandrolone; Oxandrin; Oxandrolona; Oxandrolonum; Protivar; Provitar; Vasorome; Ossandrolone [DCIT]; SC 11585; Anavar (TN); Oxandrin (TN); Oxandrolona [INN-Spanish]; Oxandrolonum [INN-Latin]; SC-11585; Oxandrin, Anavar, Oxandrolone; Oxandrolone (JAN/USP/INN); Oxandrolone [USAN:INN:BAN:JAN]; Dodecahydro-3-hydroxy-6-(hydroxy-methyl)-3,3a,6-trimethyl-1H-benz(e)indene-7-acetic acid delta-lactone; (1S,3aS,3bR,5aS,9aS,9bS,11aS)-1-hydroxy-1,9a,11a-trimethyl-2,3,3a,3b,4,5,5a,6,9,9b,10,11-dodecahydroindeno[4,5-h]isochromen-7-one; (4aS,4bS,6aS,7S,9aS,9bR,11aS)-7-hydroxy-4a,6a,7-trimethyltetradecahydroindeno[4,5-h]isochromen-2(1H)-one; 17-beta-hydroxy-17-methyl-2-oxa-androstan-3-one; 17-beta-hydroxy-17-methyl-2-oxa-androstan-3-one (9CI); 17beta-Hydroxy-17-methyl-2-oxa-5alpha-androstan-3-one; 17beta-Hydroxy-17alpha-methyl-2-oxa-5alpha-androstan-3-one; 2-Oxa-5alpha-androstan-3-one, 17beta-hydroxy-17-methyl-(8CI); 2-Oxaandrostan-3-one, 17-hydroxy-17-methyl-, (5-alpha,17-beta)-(9CI)

Indication

Disease Entry	ICD 11	Status	REF
Alcoholic hepatitis	DB94.1	Approved	[1], [2]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

306.4

Topological Polar Surface Area (xlogp)

3.7

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [3]
Bioavailability: 97% of drug becomes completely available to its intended biological destination(s) [4]
Half-life: The concentration or amount of drug in body reduced by one-half in 0.55 hours [5]
Metabolism: The drug is metabolized via renal [6]

Chemical Identifiers

Formula: C19H30O3
IUPAC Name: (1S,3aS,3bR,5aS,9aS,9bS,11aS)-1-hydroxy-1,9a,11a-trimethyl-2,3,3a,3b,4,5,5a,6,9,9b,10,11-dodecahydroindeno[4,5-h]isochromen-7-one
Canonical SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CC[C@@H]4[C@@]3(COC(=O)C4)C
InChI: InChI=1S/C19H30O3/c1-17-11-22-16(20)10-12(17)4-5-13-14(17)6-8-18(2)15(13)7-9-19(18,3)21/h12-15,21H,4-11H2,1-3H3/t12-,13+,14-,15-,17-,18-,19-/m0/s1
InChIKey: QSLJIVKCVHQPLV-PEMPUTJUSA-N

Cross-matching ID

PubChem CID: 5878
ChEBI ID: CHEBI:7820
CAS Number: 53-39-4
DrugBank ID: DB00621
TTD ID: D0U3GL
ACDINA ID: D00497

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Androgen receptor (AR)	TTS64P2	ANDR_HUMAN	Agonist	[7]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Alcoholic hepatitis

ICD Disease Classification

DB94.1

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Androgen receptor (AR)	DTT	AR	2.13E-01	-0.07	-0.11

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

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

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Increased risk of hepatotoxicity by the combination of Oxandrolone and Remdesivir.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[18]
Repaglinide	DM5SXUV	Moderate	Increased risk of hypoglycemia by the combination of Oxandrolone and Repaglinide.	Acute diabete complication [5A2Y]	[19]
Tolazamide	DMIHRNA	Moderate	Increased risk of hypoglycemia by the combination of Oxandrolone and Tolazamide.	Acute diabete complication [5A2Y]	[19]
Nateglinide	DMLK2QH	Moderate	Increased risk of hypoglycemia by the combination of Oxandrolone and Nateglinide.	Acute diabete complication [5A2Y]	[19]
Insulin-glulisine	DMQI0FU	Moderate	Increased risk of hypoglycemia by the combination of Oxandrolone and Insulin-glulisine.	Acute diabete complication [5A2Y]	[19]
Insulin-aspart	DMX7V28	Moderate	Increased risk of hypoglycemia by the combination of Oxandrolone and Insulin-aspart.	Acute diabete complication [5A2Y]	[20]
Bedaquiline	DM3906J	Moderate	Increased risk of hepatotoxicity by the combination of Oxandrolone and Bedaquiline.	Antimicrobial drug resistance [MG50-MG52]	[21]
Pexidartinib	DMS2J0Z	Major	Increased risk of hepatotoxicity by the combination of Oxandrolone and Pexidartinib.	Bone/articular cartilage neoplasm [2F7B]	[22]
Cannabidiol	DM0659E	Moderate	Increased risk of hepatotoxicity by the combination of Oxandrolone and Cannabidiol.	Epileptic encephalopathy [8A62]	[23]
Efavirenz	DMC0GSJ	Moderate	Increased risk of hepatotoxicity by the combination of Oxandrolone and Efavirenz.	Human immunodeficiency virus disease [1C60-1C62]	[24]
Fluvastatin	DM4MDJY	Moderate	Decreased metabolism of Oxandrolone caused by Fluvastatin mediated inhibition of CYP450 enzyme.	Hyper-lipoproteinaemia [5C80]	[18]
Mipomersen	DMGSRN1	Major	Increased risk of hepatotoxicity by the combination of Oxandrolone and Mipomersen.	Hyper-lipoproteinaemia [5C80]	[25]
Teriflunomide	DMQ2FKJ	Major	Increased risk of hepatotoxicity by the combination of Oxandrolone and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[26]
BMS-201038	DMQTAGO	Major	Increased risk of hepatotoxicity by the combination of Oxandrolone and BMS-201038.	Hyper-lipoproteinaemia [5C80]	[27]
Pirfenidone	DM6VZFQ	Moderate	Decreased metabolism of Oxandrolone caused by Pirfenidone mediated inhibition of CYP450 enzyme.	Idiopathic interstitial pneumonitis [CB03]	[23]
Lesinurad	DMUR64T	Moderate	Decreased metabolism of Oxandrolone caused by Lesinurad mediated inhibition of CYP450 enzyme.	Inborn purine/pyrimidine/nucleotide metabolism error [5C55]	[28]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of hepatotoxicity by the combination of Oxandrolone and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[29]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Oxandrolone and Idelalisib.	Mature B-cell leukaemia [2A82]	[30]
Clofarabine	DMCVJ86	Moderate	Increased risk of hepatotoxicity by the combination of Oxandrolone and Clofarabine.	Mature B-cell lymphoma [2A85]	[31]
Carfilzomib	DM48K0X	Major	Additive thrombogenic effects by the combination of Oxandrolone and Carfilzomib.	Multiple myeloma [2A83]	[18]
Siponimod	DM2R86O	Major	Decreased metabolism of Oxandrolone caused by Siponimod mediated inhibition of CYP450 enzyme.	Multiple sclerosis [8A40]	[18]
Lonafarnib	DMGM2Z6	Moderate	Decreased metabolism of Oxandrolone caused by Lonafarnib mediated inhibition of CYP450 enzyme.	Premature ageing appearance [LD2B]	[32]
Leflunomide	DMR8ONJ	Major	Increased risk of hepatotoxicity by the combination of Oxandrolone and Leflunomide.	Rheumatoid arthritis [FA20]	[26]
Trabectedin	DMG3Y89	Moderate	Increased risk of hepatotoxicity by the combination of Oxandrolone and Trabectedin.	Solid tumour/cancer [2A00-2F9Z]	[23]
Naltrexone	DMUL45H	Moderate	Increased risk of hepatotoxicity by the combination of Oxandrolone and Naltrexone.	Substance abuse [6C40]	[33]
Tolbutamide	DM02AWV	Moderate	Increased risk of hypoglycemia by the combination of Oxandrolone and Tolbutamide.	Type 2 diabetes mellitus [5A11]	[19]
Chlorpropamide	DMPHZQE	Moderate	Increased risk of hypoglycemia by the combination of Oxandrolone and Chlorpropamide.	Type 2 diabetes mellitus [5A11]	[19]
Insulin-detemir	DMOA4VW	Moderate	Increased risk of hypoglycemia by the combination of Oxandrolone and Insulin-detemir.	Type-1/2 diabete [5A10-5A11]	[19]
Insulin degludec	DMPL395	Moderate	Increased risk of hypoglycemia by the combination of Oxandrolone and Insulin degludec.	Type-1/2 diabete [5A10-5A11]	[19]
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⏷ Show the Full List of 29 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Oxandrolone 10 mg tablet	10 mg	Oral Tablet	Oral
Oxandrolone 2.5 mg tablet	2.5 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7092).
2	FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 076761.
3	BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
4	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
5	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6	FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
7	The effect of oxandrolone treatment on human osteoblastic cells. J Burns Wounds. 2007 Mar 7;6:e4.
8	Dehydroepiandrosterone, glucose-6-phosphate dehydrogenase, and longevity. Ageing Res Rev. 2004 Apr;3(2):171-87.
9	Androgen receptor as a target in androgen-independent prostate cancer. Urology. 2002 Sep;60(3 Suppl 1):132-8; discussion 138-9.
10	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2019
11	Molecular mechanism of androgen action. Trends Endocrinol Metab. 1998 Oct 1;9(8):317-24.
12	Ouellet M, Percival MD: Effect of inhibitor time-dependency on selectivity towards cyclooxygenase isoforms. Biochem J. 1995 Feb 15;306 ( Pt 1):247-51.
13	Androgen receptor overexpression induces tamoxifen resistance in human breast cancer cells. Breast Cancer Res Treat. 2010 May;121(1):1-11.
14	The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
15	2018 FDA drug approvals.Nat Rev Drug Discov. 2019 Feb;18(2):85-89.
16	CX3CR1 is expressed by prostate epithelial cells and androgens regulate the levels of CX3CL1/fractalkine in the bone marrow: potential role in prostate cancer bone tropism. Cancer Res. 2008 Mar 15;68(6):1715-22.
17	Expression of androgen receptor on fibroblast and hepatocyte of rats after deep second-degree burn caused by scalding. Sichuan Da Xue Xue Bao Yi Xue Ban. 2005 May;36(3):362-4.
18	Cerner Multum, Inc. "Australian Product Information.".
19	Abad S, Moachon L, Blanche P, Bavoux F, Sicard D, Salmon-Ceron D "Possible interaction between glicazide, fluconazole and sulfamethoxazole resulting in severe hypoglycaemia." Br J Clin Pharmacol 52 (2001): 456-7. [PMID: 11678792]
20	Asplund K, Wiholm BE, Lithner F "Glibenclamide-associated hypoglycaemia: a report on 57 cases." Diabetologia 24 (1983): 412-7. [PMID: 6411511]
21	Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
22	Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
23	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
24	Elsharkawy AM, Schwab U, McCarron B, et al. "Efavirenz induced acute liver failure requiring liver transplantation in a slow drug metaboliser." J Clin Virol 58 (2013): 331-3. [PMID: 23763943]
25	Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
26	Canadian Pharmacists Association.
27	Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA.
28	Product Information. Zurampic (lesinurad). Astra-Zeneca Pharmaceuticals, Wilmington, DE.
29	Al-Nawakil C, Willems L, Mauprivez C, et.al "Successful treatment of l-asparaginase-induced severe acute hepatotoxicity using mitochondrial cofactors." Leuk Lymphoma 55 (2014): 1670-4. [PMID: 24090500]
30	Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.
31	Product Information. Clolar (clofarabine). sanofi-aventis, Bridgewater, NJ.
32	Product Information. Zokinvy (lonafarnib). Eiger BioPharmaceuticals, Palo Alto, CA.
33	Product Information. ReVia (naltrexone). DuPont Pharmaceuticals, Wilmington, DE.