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

Stem definition	Drug id	CAS RN
antivirals	989	154598-52-4

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: efavirenz stocrin (-)-efavirenz sustiva	Efavirenz is a non-nucleoside reverse transcriptase (RT) inhibitor of HIV-1. Efavirenz activity is mediated predominantly by noncompetitive inhibition of HIV-1 reverse transcriptase. HIV-2 RT and human cellular DNA polymerases alpha, beta, gamma, and delta are not inhibited by efavirenz. Molecular weight: 315.68 Formula: C14H9ClF3NO2 CLOGP: 3.92 LIPINSKI: 0 HAC: 3 HDO: 1 TPSA: 38.33 ALOGS: -4.57 ROTB: 3 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

efavirenz
stocrin
(-)-efavirenz
sustiva

Efavirenz is a non-nucleoside reverse transcriptase (RT) inhibitor of HIV-1. Efavirenz activity is mediated predominantly by noncompetitive inhibition of HIV-1 reverse transcriptase. HIV-2 RT and human cellular DNA polymerases alpha, beta, gamma, and delta are not inhibited by efavirenz.

Molecular weight: 315.68
Formula: C14H9ClF3NO2
CLOGP: 3.92
LIPINSKI: 0
HAC: 3
HDO: 1
TPSA: 38.33
ALOGS: -4.57
ROTB: 3

Status: OFP

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

Drug dosage:

Dose	Unit	Route
0.60	g	O

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	42.50 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
MRTD (Maximum Recommended Therapeutic Daily Dose)	27.15 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	0.50 %	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	0.01 mg/mL	Benet LZ, Broccatelli F, Oprea TI
fu (Fraction unbound in plasma)	0.01 %	Kawashima H, Watanabe R, Esaki T, Kuroda M, Nagao C, Natsume-Kitatani Y, Ohashi R, Komura H, Mizuguchi K

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Approvals:

Date	Agency	Company	Orphan
May 28, 1999	EMA	Bristol-Myers Squibb Pharma EEIG
Sept. 17, 1998	FDA	BRISTOL MYERS SQUIBB

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
Abortion spontaneous	724.60	25.53	271	9358	46924	63432469
Viral mutation identified	622.86	25.53	122	9507	1688	63477705
Maternal exposure during pregnancy	564.34	25.53	372	9257	219690	63259703
Virologic failure	523.22	25.53	106	9523	1756	63477637
Abortion induced	443.50	25.53	129	9500	10113	63469280
Pregnancy	421.06	25.53	171	9458	36665	63442728
Immune reconstitution inflammatory syndrome	403.11	25.53	107	9522	5977	63473416
Exposure during pregnancy	388.06	25.53	259	9370	155288	63324105
Stillbirth	378.15	25.53	104	9525	6646	63472747
Drug resistance	334.18	25.53	127	9502	22806	63456587

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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
Depression	1393.23	16.72	798	19329	96300	34840504
Drug interaction	1025.54	16.72	920	19207	225026	34711778
Immune reconstitution inflammatory syndrome	896.18	16.72	291	19836	8468	34928336
Viral mutation identified	760.90	16.72	201	19926	2753	34934051
Virologic failure	737.51	16.72	203	19924	3277	34933527
Lipodystrophy acquired	616.86	16.72	175	19952	3169	34933635
Pathogen resistance	577.63	16.72	214	19913	9268	34927536
Psychiatric decompensation	363.83	16.72	113	20014	2824	34933980
Mitochondrial toxicity	314.07	16.72	99	20028	2600	34934204
Loss of personal independence in daily activities	301.46	16.72	205	19922	32974	34903830

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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
Immune reconstitution inflammatory syndrome	1350.09	16.73	379	22844	13462	79707703
Depression	859.34	16.73	617	22606	216173	79504992
Viral mutation identified	796.99	16.73	192	23031	3666	79717499
Drug interaction	776.27	16.73	765	22458	414418	79306747
Virologic failure	745.85	16.73	185	23038	4006	79717159
Lipodystrophy acquired	745.07	16.73	186	23037	4139	79717026
Drug resistance	571.67	16.73	268	22955	41945	79679220
Pathogen resistance	457.42	16.73	168	23055	14174	79706991
Abortion spontaneous	448.35	16.73	203	23020	29304	79691861
Psychiatric decompensation	401.84	16.73	112	23111	3851	79717314

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	J05AG03	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Non-nucleoside reverse transcriptase inhibitors
ATC	J05AR06	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations
ATC	J05AR11	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	N0000182140	Cytochrome P450 2C19 Inhibitors
FDA MoA	N0000182141	Cytochrome P450 3A4 Inhibitors

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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
Prevention of HIV Infection after Exposure	off-label use
Osteomalacia	contraindication	4598005	DOID:10573
Hypophosphatemia	contraindication	4996001
Suicidal thoughts	contraindication	6471006
Hypercholesterolemia	contraindication	13644009
Depressive disorder	contraindication	35489007
Fanconi syndrome	contraindication	40488004	DOID:1062
Hypokalemia	contraindication	43339004
Cardiovascular disease	contraindication	49601007	DOID:1287

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	10.6	acidic

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
600MG;200MG;300MG	ATRIPLA	GILEAD SCIENCES	N021937	July 12, 2006	RX	TABLET	ORAL	8592397	Jan. 13, 2024	TREATMENT OF HIV-1 INFECTION IN ADULTS
600MG;200MG;300MG	ATRIPLA	GILEAD SCIENCES	N021937	July 12, 2006	RX	TABLET	ORAL	8592397	Jan. 13, 2024	TREATMENT OF HIV-1 INFECTION IN PEDIATRIC PATIENTS 12 YEARS OF AGE AND OLDER
600MG;200MG;300MG	ATRIPLA	GILEAD SCIENCES	N021937	July 12, 2006	RX	TABLET	ORAL	8716264	Jan. 13, 2024	TREATMENT OF HIV INFECTION
600MG;200MG;300MG	ATRIPLA	GILEAD SCIENCES	N021937	July 12, 2006	RX	TABLET	ORAL	9457036	Jan. 13, 2024	TREATMENT OF HIV INFECTION
600MG;200MG;300MG	ATRIPLA	GILEAD SCIENCES	N021937	July 12, 2006	RX	TABLET	ORAL	9744181	Jan. 13, 2024	TREATMENT OF HIV INFECTION
600MG;200MG;300MG	ATRIPLA	GILEAD SCIENCES	N021937	July 12, 2006	RX	TABLET	ORAL	9018192	June 13, 2026	TREATMENT OF HIV-1 INFECTION IN ADULTS
600MG;200MG;300MG	ATRIPLA	GILEAD SCIENCES	N021937	July 12, 2006	RX	TABLET	ORAL	9018192	June 13, 2026	TREATMENT OF HIV-1 INFECTION IN PEDIATRIC PATIENTS 12 YEARS OF AGE AND OLDER
600MG;200MG;300MG	ATRIPLA	GILEAD SCIENCES	N021937	July 12, 2006	RX	TABLET	ORAL	9545414	June 13, 2026	TREATMENT OF HIV-1 INFECTION IN ADULTS
600MG;200MG;300MG	ATRIPLA	GILEAD SCIENCES	N021937	July 12, 2006	RX	TABLET	ORAL	9545414	June 13, 2026	TREATMENT OF HIV-1 INFECTION IN PEDIATRIC PATIENTS 12 YEARS OF AGE AND OLDER

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Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Nuclear receptor subfamily 1 group I member 2	Nuclear hormone receptor	O75469	NR1I2_HUMAN				WOMBAT-PK
ATP-binding cassette sub-family G member 2	Transporter	Q9UNQ0	ABCG2_HUMAN		IC50	4.69	CHEMBL
Cholesterol 24-hydroxylase	Enzyme	Q9Y6A2	CP46A_HUMAN		Kd	6.10	CHEMBL
Cytochrome P450 3A4	Enzyme	P08684	CP3A4_HUMAN	INHIBITOR	IC50	4.76	IUPHAR
Reverse transcriptase/RNaseH	Enzyme		Q72547_9HIV1	INHIBITOR	Ki	8.52	CHEMBL	CHEMBL
Gag-Pol polyprotein	Polyprotein		POL_HV1A2	INHIBITOR	IC50	8.30	WOMBAT-PK
Reverse transcriptase	Enzyme		Q9WKE8_9HIV1		IC50	8.89	CHEMBL
Reverse transcriptase protein	Unclassified		Q9WJQ2_9HIV1		Ki	8.07	CHEMBL
Envelope glycoprotein gp160 [Cleaved into: Surface protein gp120	Unclassified		Q6QLK5_9HIV1		IC50	8.46	CHEMBL

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External reference:

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ID	Source
EFZ	PDB_CHEM_ID
007651	NDDF
11287	IUPHAR_LIGAND_ID
116078005	SNOMEDCT_US
11884	MMSL
195084	RXNORM
210786	MMSL
387001004	SNOMEDCT_US
4021133	VUID
4021133	VANDF

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Atripla	HUMAN PRESCRIPTION DRUG LABEL	3	15584-0101	TABLET, FILM COATED	600 mg	ORAL	NDA	34 sections
Atripla	HUMAN PRESCRIPTION DRUG LABEL	3	53808-0208	TABLET, FILM COATED	600 mg	ORAL	NDA	31 sections
Atripla	HUMAN PRESCRIPTION DRUG LABEL	3	54868-5643	TABLET, FILM COATED	600 mg	ORAL	NDA	31 sections
Atripla Access	HUMAN PRESCRIPTION DRUG LABEL	3	61958-1601	TABLET, FILM COATED	600 mg	ORAL	EXPORT ONLY	34 sections
Efavirenz	HUMAN PRESCRIPTION DRUG LABEL	1	0378-2233	TABLET, FILM COATED	600 mg	ORAL	ANDA	26 sections
Efavirenz	Human Prescription Drug Label	1	31722-504	TABLET, FILM COATED	600 mg	ORAL	ANDA	28 sections
Efavirenz	Human Prescription Drug Label	1	31722-504	TABLET, FILM COATED	600 mg	ORAL	ANDA	28 sections
Efavirenz	HUMAN PRESCRIPTION DRUG LABEL	1	42543-889	TABLET	600 mg	ORAL	ANDA	26 sections
Efavirenz	HUMAN PRESCRIPTION DRUG LABEL	1	42543-889	TABLET	600 mg	ORAL	ANDA	26 sections
Efavirenz	HUMAN PRESCRIPTION DRUG LABEL	1	51407-382	TABLET	600 mg	ORAL	ANDA	26 sections

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