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

Stem definitionDrug idCAS RN
antivirals 989 154598-52-4

Description:

MoleculeDescription

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: 3.73
  • 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:

DoseUnitRoute
0.60 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.01 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 27.15 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 42.50 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Sept. 17, 1998 FDA BRISTOL MYERS SQUIBB

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Maternal exposure during pregnancy 1019.11 57.19 245 1507 14618 2341715
Abortion spontaneous 693.01 57.19 177 1575 13268 2343065
Pregnancy 677.08 57.19 157 1595 7792 2348541
Exposure during pregnancy 501.63 57.19 158 1594 25061 2331272
Immune reconstitution inflammatory syndrome 469.95 57.19 85 1667 1159 2355174
Abortion induced 462.47 57.19 99 1653 3337 2352996
Stillbirth 451.08 57.19 84 1668 1357 2354976
Normal newborn 395.40 57.19 74 1678 1226 2355107
Viral mutation identified 374.47 57.19 56 1696 199 2356134
Drug resistance 372.04 57.19 79 1673 2545 2353788
Foetal exposure during pregnancy 312.45 57.19 78 1674 5174 2351159
Virologic failure 285.77 57.19 45 1707 241 2356092
Live birth 265.58 57.19 53 1699 1238 2355095
Lactic acidosis 204.74 57.19 56 1696 5274 2351059
Caesarean section 175.99 57.19 47 1705 4034 2352299
Anaemia 158.54 57.19 75 1677 34717 2321616
Cerebellar ataxia 131.05 57.19 22 1730 184 2356149
Premature delivery 129.15 57.19 35 1717 3165 2353168
Birth mark 122.70 57.19 17 1735 28 2356305
Congenital umbilical hernia 118.10 57.19 17 1735 42 2356291
Lipodystrophy acquired 90.54 57.19 17 1735 282 2356051
Premature baby 88.19 57.19 26 1726 3178 2353155
Pyrexia 87.30 57.19 59 1693 53649 2302684
Pregnancy on contraceptive 83.25 57.19 16 1736 302 2356031
Hepatitis fulminant 82.76 57.19 18 1734 639 2355694
Pathogen resistance 78.29 57.19 18 1734 825 2355508
Foetal death 77.49 57.19 21 1731 1891 2354442
Pulmonary tuberculosis 77.42 57.19 18 1734 867 2355466
Tuberculosis 77.24 57.19 21 1731 1914 2354419
Autoimmune hepatitis 70.48 57.19 19 1733 1676 2354657
Product use issue 70.12 57.19 31 1721 12138 2344195
Vomiting 70.01 57.19 58 1694 71544 2284789
Encephalopathy 67.23 57.19 23 1729 4538 2351795
Treatment noncompliance 62.88 57.19 23 1729 5511 2350822
Premature rupture of membranes 61.43 57.19 15 1737 891 2355442
Drug level increased 61.15 57.19 19 1733 2768 2353565
Rash 59.72 57.19 49 1703 59509 2296824
Drug interaction 59.43 57.19 37 1715 29126 2327207
Jaundice 59.29 57.19 22 1730 5486 2350847
Immune reconstitution inflammatory syndrome associated tuberculosis 59.02 57.19 9 1743 37 2356296
Pregnancy with implant contraceptive 58.64 57.19 13 1739 504 2355829

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Immune reconstitution inflammatory syndrome 1191.32 40.97 220 2299 1329 1742933
Lipodystrophy acquired 644.93 40.97 106 2413 267 1743995
Drug resistance 392.18 40.97 101 2418 3129 1741133
Foetal exposure during pregnancy 358.56 40.97 109 2410 6250 1738012
Mitochondrial toxicity 276.01 40.97 47 2472 155 1744107
Hyperlipidaemia 271.67 40.97 70 2449 2159 1742103
Pyrexia 258.38 40.97 152 2367 46248 1698014
Viral mutation identified 234.14 40.97 45 2474 333 1743929
Virologic failure 224.80 40.97 44 2475 362 1743900
Progressive external ophthalmoplegia 222.07 40.97 33 2486 27 1744235
Lipoatrophy 186.78 40.97 31 2488 83 1744179
Eyelid ptosis 182.19 40.97 41 2478 696 1743566
Hyperlactacidaemia 177.56 40.97 36 2483 360 1743902
Pulmonary tuberculosis 167.14 40.97 41 2478 1025 1743237
Anaemia 159.16 40.97 95 2424 29362 1714900
Depression 145.86 40.97 74 2445 16595 1727667
Hepatitis 141.64 40.97 51 2468 4904 1739358
Alanine aminotransferase increased 138.90 40.97 65 2454 12213 1732049
Diplopia 135.63 40.97 42 2477 2528 1741734
Hepatic function abnormal 134.30 40.97 54 2465 7020 1737242
Aspartate aminotransferase increased 131.16 40.97 60 2459 10696 1733566
Rash 130.75 40.97 93 2426 38600 1705662
Diarrhoea 121.94 40.97 102 2417 53750 1690512
Gamma-glutamyltransferase increased 121.81 40.97 46 2473 5052 1739210
Vomiting 120.05 40.97 88 2431 38227 1706035
Lactic acidosis 114.33 40.97 44 2475 5085 1739177
Gynaecomastia 113.13 40.97 35 2484 2097 1742165
Drug-induced liver injury 110.33 40.97 38 2481 3199 1741063
Lymphadenopathy 108.79 40.97 40 2479 4074 1740188
Abnormal dreams 108.64 40.97 33 2486 1858 1742404
Hypertriglyceridaemia 104.57 40.97 29 2490 1180 1743082
Hepatic fibrosis 102.77 40.97 25 2494 601 1743661
Acute kidney injury 102.05 40.97 77 2442 34867 1709395
Meningitis cryptococcal 100.54 40.97 22 2497 325 1743937
Renal impairment 99.84 40.97 52 2467 12262 1732000
Blood triglycerides increased 94.36 40.97 32 2487 2568 1741694
Drug interaction 93.73 40.97 67 2452 27891 1716371
General physical health deterioration 85.66 40.97 48 2471 13070 1731192
Hepatotoxicity 85.26 40.97 31 2488 3053 1741209
Nervous system disorder 84.34 40.97 29 2490 2425 1741837
Premature baby 82.93 40.97 30 2489 2912 1741350
Blood alkaline phosphatase increased 82.70 40.97 35 2484 5160 1739102
Kaposi's sarcoma 80.52 40.97 22 2497 845 1743417
Hypercholesterolaemia 77.58 40.97 23 2496 1189 1743073
Nightmare 76.98 40.97 28 2491 2759 1741503
Portal hypertension 75.95 40.97 20 2499 666 1743596
Blood HIV RNULL increased 75.81 40.97 16 2503 197 1744065
Jaundice 74.34 40.97 34 2485 6028 1738234
Proteinuria 72.73 40.97 27 2492 2817 1741445
Weight decreased 72.67 40.97 53 2466 22700 1721562
Asthenia 72.66 40.97 63 2456 34607 1709655
Treatment failure 71.19 40.97 30 2489 4371 1739891
Insomnia 71.08 40.97 46 2473 16230 1728032
Nausea 71.02 40.97 74 2445 51122 1693140
Hepatomegaly 70.12 40.97 23 2496 1662 1742600
Cholestasis 69.52 40.97 28 2491 3637 1740625
Nephropathy toxic 69.49 40.97 23 2496 1709 1742553
Pneumocystis jirovecii pneumonia 69.04 40.97 25 2494 2431 1741831
Cachexia 68.17 40.97 20 2499 996 1743266
Liver disorder 67.18 40.97 31 2488 5605 1738657
Pathogen resistance 66.80 40.97 20 2499 1069 1743193
Cytomegalovirus chorioretinitis 66.05 40.97 16 2503 377 1743885
Renal failure 64.73 40.97 47 2472 19970 1724292
Cryptococcosis 64.21 40.97 15 2504 301 1743961
Osteonecrosis 64.05 40.97 27 2492 3935 1740327
Tuberculosis 63.90 40.97 22 2497 1844 1742418
Neuropathy peripheral 63.47 40.97 35 2484 9218 1735044
Mycobacterium avium complex infection 63.21 40.97 15 2504 323 1743939
HIV infection 61.47 40.97 14 2505 250 1744012
Headache 61.18 40.97 57 2462 34319 1709943
Diabetes mellitus 61.18 40.97 31 2488 6877 1737385
Dyspnoea 59.51 40.97 68 2451 51991 1692271
Hepatitis B 57.76 40.97 19 2500 1384 1742878
Decreased appetite 57.38 40.97 47 2472 23824 1720438
Hypertension 56.89 40.97 43 2476 19405 1724857
Hepatic cirrhosis 56.35 40.97 22 2497 2631 1741631
Abdominal pain 55.21 40.97 44 2475 21446 1722816
Hypophosphataemia 55.00 40.97 18 2501 1290 1742972
Oral candidiasis 54.99 40.97 18 2501 1291 1742971
CD4 lymphocytes decreased 54.36 40.97 14 2505 426 1743836
Hepatosplenomegaly 53.77 40.97 15 2504 622 1743640
Immune reconstitution inflammatory syndrome associated tuberculosis 53.18 40.97 9 2510 28 1744234
Liver injury 52.29 40.97 19 2500 1863 1742399
Ophthalmoplegia 52.08 40.97 12 2507 226 1744036
Hypokalaemia 51.80 40.97 27 2492 6347 1737915
Intracranial pressure increased 51.29 40.97 15 2504 738 1743524
Meningitis tuberculous 50.73 40.97 10 2509 85 1744177
Viral load increased 50.43 40.97 14 2505 570 1743692
Hepatic steatosis 49.88 40.97 20 2499 2564 1741698
Renal tubular disorder 49.07 40.97 15 2504 860 1743402
Blood lactic acid increased 48.67 40.97 15 2504 884 1743378
Sepsis 48.21 40.97 39 2480 19399 1724863
Myocardial infarction 48.17 40.97 45 2474 27129 1717133
Amylase increased 47.72 40.97 16 2503 1236 1743026
Developmental hip dysplasia 47.71 40.97 9 2510 59 1744203
Sleep disorder 47.31 40.97 22 2497 4041 1740221
Confusional state 47.17 40.97 40 2479 21238 1723024
HIV-associated neurocognitive disorder 46.95 40.97 9 2510 65 1744197
Congenital umbilical hernia 46.83 40.97 9 2510 66 1744196
Oesophageal candidiasis 46.23 40.97 13 2506 555 1743707
Blood creatine phosphokinase increased 46.07 40.97 28 2491 8828 1735434
Liver transplant 45.40 40.97 13 2506 593 1743669
Nodular regenerative hyperplasia 45.23 40.97 10 2509 155 1744107
Malaise 44.95 40.97 45 2474 29520 1714742
Dizziness 44.53 40.97 48 2471 34313 1709949
Progressive multifocal leukoencephalopathy 43.50 40.97 16 2503 1623 1742639
Low density lipoprotein increased 43.44 40.97 14 2505 955 1743307
Fanconi syndrome 42.86 40.97 11 2508 330 1743932
Psychotic disorder 42.74 40.97 22 2497 5034 1739228
Hepatitis C 41.68 40.97 18 2501 2778 1741484
Exposure during pregnancy 41.56 40.97 18 2501 2799 1741463
Dyslipidaemia 41.44 40.97 13 2506 812 1743450

Pharmacologic Action:

SourceCodeDescription
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
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 N0000190118 Cytochrome P450 3A Inducers
FDA MoA N0000187064 Cytochrome P450 2B6 Inducers
FDA MoA N0000185504 Cytochrome P450 2C9 Inhibitors
FDA MoA N0000182140 Cytochrome P450 2C19 Inhibitors
FDA MoA N0000182141 Cytochrome P450 3A4 Inhibitors
CHEBI has role CHEBI:36044 antiviral drug
MeSH PA D000890 Anti-Infective Agents
MeSH PA D044966 Anti-Retroviral Agents
MeSH PA D000998 Antiviral Agents
MeSH PA D065695 Cytochrome P-450 CYP2B6 Inducers
MeSH PA D065689 Cytochrome P-450 CYP2C19 Inhibitors
MeSH PA D065688 Cytochrome P-450 CYP2C9 Inhibitors
MeSH PA D065701 Cytochrome P-450 CYP3A Inducers
MeSH PA D065607 Cytochrome P-450 Enzyme Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D065606 Metabolic Side Effects of Drugs and Substances
MeSH PA D019384 Nucleic Acid Synthesis Inhibitors
MeSH PA D018894 Reverse Transcriptase Inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
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
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Aggressive behavior contraindication 61372001
Chronic type B viral hepatitis contraindication 61977001
Kidney disease contraindication 90708001 DOID:557
Lactic acidosis contraindication 91273001 DOID:3650
Chronic hepatitis C contraindication 128302006
Seizure disorder contraindication 128613002
Liver function tests abnormal contraindication 166603001
Paranoid disorder contraindication 191667009
Steatosis of liver contraindication 197321007
Mania contraindication 231494001
Disease of liver contraindication 235856003 DOID:409
Pathological fracture contraindication 268029009
Pregnancy, function contraindication 289908002
Hypertriglyceridemia contraindication 302870006
Osteopenia contraindication 312894000
Breastfeeding (mother) contraindication 413712001
Obesity contraindication 414916001 DOID:9970

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.6 acidic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
600MG ATRIPLA GILEAD SCIENCES N021937 July 12, 2006 RX TABLET ORAL 6642245 Nov. 4, 2020 TREATMENT OF HIV-1 INFECTION IN ADULTS
600MG ATRIPLA GILEAD SCIENCES N021937 July 12, 2006 RX TABLET ORAL 6642245 Nov. 4, 2020 TREATMENT OF HIV-1 INFECTION IN PEDIATRIC PATIENTS 12 YEARS OF AGE AND OLDER
600MG ATRIPLA GILEAD SCIENCES N021937 July 12, 2006 RX TABLET ORAL 8592397 Jan. 13, 2024 TREATMENT OF HIV-1 INFECTION IN ADULTS
600MG 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 ATRIPLA GILEAD SCIENCES N021937 July 12, 2006 RX TABLET ORAL 8716264 Jan. 13, 2024 TREATMENT OF HIV INFECTION
600MG ATRIPLA GILEAD SCIENCES N021937 July 12, 2006 RX TABLET ORAL 9457036 Jan. 13, 2024 TREATMENT OF HIV INFECTION
600MG ATRIPLA GILEAD SCIENCES N021937 July 12, 2006 RX TABLET ORAL 9744181 Jan. 13, 2024 TREATMENT OF HIV INFECTION
600MG ATRIPLA GILEAD SCIENCES N021937 July 12, 2006 RX TABLET ORAL 9018192 June 13, 2026 TREATMENT OF HIV-1 INFECTION IN ADULTS
600MG 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 ATRIPLA GILEAD SCIENCES N021937 July 12, 2006 RX TABLET ORAL 9545414 June 13, 2026 TREATMENT OF HIV-1 INFECTION IN ADULTS
600MG 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

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Nuclear receptor subfamily 1 group I member 2 Nuclear hormone receptor WOMBAT-PK
Reverse transcriptase/RNaseH Enzyme INHIBITOR Ki 8.52 CHEMBL CHEMBL
Gag-Pol polyprotein Polyprotein INHIBITOR IC50 8.30 WOMBAT-PK
Reverse transcriptase Enzyme IC50 8.89 CHEMBL

External reference:

IDSource
4021133 VUID
N0000148587 NUI
C0674428 UMLSCUI
D00896 KEGG_DRUG
116078005 SNOMEDCT_US
d04355 MMSL
7492 MMSL
195085 RXNORM
4021133 VANDF
387001004 SNOMEDCT_US
007651 NDDF
210786 MMSL
CHEMBL223228 ChEMBL_ID
DB00625 DRUGBANK_ID
JE6H2O27P8 UNII
7718 INN_ID
EFZ PDB_CHEM_ID
CHEBI:119486 CHEBI
64139 PUBCHEM_CID
C098320 MESH_SUPPLEMENTAL_RECORD_UI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
SUSTIVA HUMAN PRESCRIPTION DRUG LABEL 1 0056-0470 CAPSULE, GELATIN COATED 50 mg ORAL NDA 20 sections
SUSTIVA HUMAN PRESCRIPTION DRUG LABEL 1 0056-0474 CAPSULE, GELATIN COATED 200 mg ORAL NDA 20 sections
SUSTIVA HUMAN PRESCRIPTION DRUG LABEL 1 0056-0510 TABLET, FILM COATED 600 mg ORAL NDA 20 sections
Efavirenz HUMAN PRESCRIPTION DRUG LABEL 1 0378-2233 TABLET, FILM COATED 600 mg ORAL ANDA 18 sections
Atripla HUMAN PRESCRIPTION DRUG LABEL 3 15584-0101 TABLET, FILM COATED 600 mg ORAL NDA 20 sections
Efavirenz HUMAN PRESCRIPTION DRUG LABEL 1 31722-504 TABLET, FILM COATED 600 mg ORAL ANDA 18 sections
SYMFI LO HUMAN PRESCRIPTION DRUG LABEL 3 49502-425 TABLET, FILM COATED 400 mg ORAL NDA 19 sections
SYMFI HUMAN PRESCRIPTION DRUG LABEL 3 49502-475 TABLET, FILM COATED 600 mg ORAL NDA 19 sections
Atripla HUMAN PRESCRIPTION DRUG LABEL 3 53808-0208 TABLET, FILM COATED 600 mg ORAL NDA 20 sections
SUSTIVA HUMAN PRESCRIPTION DRUG LABEL 1 54868-4668 TABLET, FILM COATED 600 mg ORAL NDA 18 sections
Atripla HUMAN PRESCRIPTION DRUG LABEL 3 54868-5643 TABLET, FILM COATED 600 mg ORAL NDA 20 sections
Atripla Access HUMAN PRESCRIPTION DRUG LABEL 3 61958-1601 TABLET, FILM COATED 600 mg ORAL EXPORT ONLY 20 sections
Efavirenz HUMAN PRESCRIPTION DRUG LABEL 1 64380-889 TABLET 600 mg ORAL ANDA 18 sections
Efavirenz HUMAN PRESCRIPTION DRUG LABEL 1 64980-406 CAPSULE 50 mg ORAL ANDA 18 sections
Efavirenz HUMAN PRESCRIPTION DRUG LABEL 1 64980-407 CAPSULE 200 mg ORAL ANDA 18 sections
Efavirenz HUMAN PRESCRIPTION DRUG LABEL 1 65862-049 TABLET, FILM COATED 600 mg ORAL ANDA 18 sections
Efavirenz HUMAN PRESCRIPTION DRUG LABEL 1 65862-104 CAPSULE 50 mg ORAL ANDA 18 sections
Efavirenz HUMAN PRESCRIPTION DRUG LABEL 1 65862-105 CAPSULE 100 mg ORAL ANDA 18 sections
Efavirenz HUMAN PRESCRIPTION DRUG LABEL 1 65862-106 CAPSULE 200 mg ORAL ANDA 18 sections
Efavirenz HUMAN PRESCRIPTION DRUG LABEL 1 65862-774 TABLET, FILM COATED 600 mg ORAL ANDA 18 sections
Efavirenz HUMAN PRESCRIPTION DRUG LABEL 1 69097-301 TABLET, FILM COATED 600 mg ORAL ANDA 18 sections
Atripla HUMAN PRESCRIPTION DRUG LABEL 3 70518-0341 TABLET, FILM COATED 600 mg ORAL NDA 20 sections
Efavirenz HUMAN PRESCRIPTION DRUG LABEL 1 70518-1013 TABLET, FILM COATED 600 mg ORAL ANDA 18 sections
Efavirenz HUMAN PRESCRIPTION DRUG LABEL 1 70518-1100 TABLET 600 mg ORAL ANDA 18 sections