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nevirapine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
antivirals	1904	129618-40-2

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: nevirapine hemihydrate nevirapine viramune nevarapine	A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV INFECTIONS and AIDS. Molecular weight: 266.30 Formula: C15H14N4O CLOGP: 2.72 LIPINSKI: 0 HAC: 5 HDO: 1 TPSA: 58.12 ALOGS: -3.41 ROTB: 1 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

nevirapine hemihydrate
nevirapine
viramune
nevarapine

A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV INFECTIONS and AIDS.

Molecular weight: 266.30
Formula: C15H14N4O
CLOGP: 2.72
LIPINSKI: 0
HAC: 5
HDO: 1
TPSA: 58.12
ALOGS: -3.41
ROTB: 1

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
0.40	g	O

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	93 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
t_half (Half-life)	53 hours	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	21.46 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
Vd (Volume of distribution)	1.30 L/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.32 %	Lombardo F, Berellini G, Obach RS
CL (Clearance)	0.30 mL/min/kg	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.10 mg/mL	Benet LZ, Broccatelli F, Oprea TI

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Approvals:

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Date	Agency	Company	Orphan
Feb. 4, 1998	EMA	Boehringer Ingelheim International GmbH
June 21, 1996	FDA	BOEHRINGER INGELHEIM

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FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Drug resistance	721.71	29.43	223	8946	22710	63457143
Viral mutation identified	678.39	29.43	130	9039	1680	63478173
Exposure during pregnancy	645.08	29.43	352	8817	155195	63324658
Abortion spontaneous	595.98	29.43	232	8937	46963	63432890
Virologic failure	570.57	29.43	113	9056	1749	63478104
Stillbirth	567.41	29.43	142	9027	6608	63473245
Foetal exposure during pregnancy	474.70	29.43	177	8992	31785	63448068
Pregnancy	314.32	29.43	137	9032	36699	63443154
Pathogen resistance	309.74	29.43	87	9082	6311	63473542
Caesarean section	284.69	29.43	103	9066	16929	63462924

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Lipodystrophy acquired	797.94	19.27	191	11231	3153	34942356
Foetal exposure during pregnancy	654.74	19.27	295	11127	37806	34907703
Mitochondrial toxicity	627.46	19.27	151	11271	2548	34942961
Virologic failure	526.19	19.27	138	11284	3342	34942167
Eyelid ptosis	509.43	19.27	150	11272	5616	34939893
Viral mutation identified	479.74	19.27	124	11298	2830	34942679
Diplopia	342.29	19.27	147	11275	16696	34928813
Progressive external ophthalmoplegia	342.22	19.27	82	11340	1353	34944156
Exposure during pregnancy	289	19.27	109	11313	8825	34936684
Pathogen resistance	279.12	19.27	108	11314	9374	34936135

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Lipodystrophy acquired	1062.26	19.45	227	14229	4098	79725834
Virologic failure	811.55	19.45	181	14275	4010	79725922
Mitochondrial toxicity	796.14	19.45	169	14287	2945	79726987
Viral mutation identified	732.64	19.45	164	14292	3694	79726238
Drug resistance	652.40	19.45	256	14200	41957	79687975
Abortion spontaneous	541.88	19.45	203	14253	29304	79700628
Eyelid ptosis	495.91	19.45	149	14307	10895	79719037
Stillbirth	424.70	19.45	106	14350	3849	79726083
Progressive external ophthalmoplegia	395.45	19.45	83	14373	1362	79728570
Exposure during pregnancy	392.14	19.45	238	14218	100894	79629038

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	J05AG01	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Non-nucleoside reverse transcriptase inhibitors
ATC	J05AR05	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations
ATC	J05AR07	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations
CHEBI has role	CHEBI:36044	antiviral drugs
CHEBI has role	CHEBI:53756	reverse transcriptase inhibitors
FDA EPC	N0000175463	Human Immunodeficiency Virus 1 Non-Nucleoside Analog Reverse Transcriptase Inhibitor
FDA EXT	N0000175460	Non-Nucleoside Analog
FDA MoA	N0000009948	Non-Nucleoside Reverse Transcriptase Inhibitors
FDA MoA	N0000187064	Cytochrome P450 2B6 Inducers
FDA MoA	N0000190118	Cytochrome P450 3A Inducers

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Human immunodeficiency virus infection	indication	86406008	DOID:526
Lyell's toxic epidermal necrolysis, subepidermal type	contraindication	23067006
Viral hepatitis C	contraindication	50711007	DOID:1883
Acute nephropathy	contraindication	58574008
Hepatic failure	contraindication	59927004
Chronic type B viral hepatitis	contraindication	61977001
Stevens-Johnson syndrome	contraindication	73442001	DOID:0050426
Chronic hepatitis C	contraindication	128302006
Liver function tests abnormal	contraindication	166603001
Disease of liver	contraindication	235856003	DOID:409

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

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Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	9.01	acidic
pKa2	2.45	Basic
pKa3	1.74	Basic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
400MG	VIRAMUNE XR	BOEHRINGER INGELHEIM	N201152	March 25, 2011	RX	TABLET, EXTENDED RELEASE	ORAL	8460704	March 12, 2029	TREATMENT OF HIV-1 BY ONCE DAILY ADMINISTRATION

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Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Reverse transcriptase/RNaseH	Enzyme	Q72547_9HIV1	INHIBITOR	Ki	6.40	CHEMBL	CHEMBL
Gag-Pol polyprotein	Polyprotein	POL_HV1A2		IC50	7.10	WOMBAT-PK
Pol polyprotein	Enzyme	Q72874_9HIV1		IC50	7	CHEMBL
Reverse transcriptase	Enzyme	Q9WKE8_9HIV1		IC50	6.30	CHEMBL
Reverse transcriptase protein	Unclassified	Q9WJQ2_9HIV1		Ki	5.40	CHEMBL

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External reference:

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ID	Source
NEV	PDB_CHEM_ID
006062	NDDF
108704001	SNOMEDCT_US
12676	IUPHAR_LIGAND_ID
175112	MMSL
220988-26-1	SECONDARY_CAS_RN
224890	RXNORM
386898005	SNOMEDCT_US
4020991	VUID
4020991	VANDF

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Nevirapine	HUMAN PRESCRIPTION DRUG LABEL	1	0378-4050	TABLET	200 mg	ORAL	ANDA	29 sections
Nevirapine	HUMAN PRESCRIPTION DRUG LABEL	1	0378-4890	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	29 sections
Nevirapine	HUMAN PRESCRIPTION DRUG LABEL	1	0378-4890	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	29 sections
Nevirapine	HUMAN PRESCRIPTION DRUG LABEL	1	0378-6950	TABLET, EXTENDED RELEASE	100 mg	ORAL	ANDA	29 sections
Nevirapine	HUMAN PRESCRIPTION DRUG LABEL	1	0781-5893	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	29 sections
Nevirapine	Human Prescription Drug Label	1	31722-505	TABLET	200 mg	ORAL	ANDA	29 sections
Nevirapine	Human Prescription Drug Label	1	31722-505	TABLET	200 mg	ORAL	ANDA	29 sections
Nevirapine	Human Prescription Drug Label	1	33342-004	TABLET	200 mg	ORAL	ANDA	28 sections
Nevirapine	Human Prescription Drug Label	1	33342-004	TABLET	200 mg	ORAL	ANDA	28 sections
Nevirapine	Human Prescription Drug Label	1	33342-004	TABLET	200 mg	ORAL	ANDA	28 sections

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