Basic information
- Standard SMILES
Cc1ccnc2c1NC(=O)c1cccnc1N2C1CC1- InChIKey
NQDJXKOVJZTUJA-UHFFFAOYSA-N- Molecular formula
- C15H14N4O
- Average molar mass
- 266.3 g/mol
- Monoisotopic mass
- 266.11676108
Names & identifiers
- Preferred name
- Nevirapine
- IUPAC
- 2-cyclopropyl-7-methyl-2,4,9,15-tetrazatricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14-hexaen-10-one
- English name
- Nevirapine
- Molecular formula
- C15H14N4O
- Molecular weight
- 266.3
Names & synonyms
Show more names
Database identifiers
- CAS
129618-40-2- PubChem CID
- 4463
- DTXSID
DTXSID7031797- ChEMBL
CHEMBL57- ChEBI
CHEBI:63613- UNII
- 99DK7FVK1H
- EC Number
- 603-345-0
- Nikkaji
- J420.601K
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 58.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 397
Physicochemical properties
- Melting point
- 247 °C · 247°C
- Boiling point
- 409.5 °C · 409.5°C (rough estimate)
- Density
- 1.13 · 1.1300 (rough estimate)
- refractive index
- 1.62 · 1.6200 (estimate)
- Flash point
- 9 ℃ · 9℃
- storage temp.
- 2 · 2-8°C
- solubility
- 22 mg/mL · DMSO: ≥22mg/mL
- form
- powder
- pka
- 2.8 · 2.8(at 25℃)
- color
- white to tan
- Water Solubility
- 0.1 g/L · 0.1g/L(temperature not stated)
- Merck
- 14 · 14,6490
- BCS Class
- 2 · 2
- Major Application
- pharmaceutical (small molecule)
- InChI
- 1S/C15H14N4O/c1-9-6-8-17-14-12(9)18-15(20)11-3-2-7-16-13(11)19(14)10-4-5-10/h2-3,6-8,10H,4-5H2,1H3,(H,18,20)
- InChIKey
- NQDJXKOVJZTUJA-UHFFFAOYSA-N
- SMILES
- CC1=CC=NC2=C1NC(C(C=CC=N3)=C3N2C4CC4)=O
- Toxicology and Carcinogenesis
- 3 · Toxicology and Carcinogenesis Studies of Mixtures of 3'-Azido-3'-Deoxythymidine (AZT), Lamivudine (3TC), Nevirapine (NVP), and Nelfinavir Mesylate (NFV) (CASRNs 30516-87-1, 134678-17-4, 129618-40-2, 159989-65-8) in B6C3F1 Mice (Transplacental Exposure Studies)
- CAS DataBase Reference
- 129618 · 129618-40-2(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 99 DK7FVK1H · 99DK7FVK1H
- NCI Drug Dictionary
- nevirapine
- ATC code
- 5 AG01 · J05AG01
- EPA Substance Registry System
- 6 H-Dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one, · 6H-Dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one, 11-cyclopropyl-5,11-dihydro-4-methyl- (129618-40-2)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 77 · NA.77
- Protein binding
- 60 % · 60%
- Excreted unchanged in urine
- 3 % · <3%
- Volume of distribution
- 1.12 · 1.12-1.3(L/kg)
- Biological half-life
- 45 · 45 (single dose) 25-30 (multiple dosing) / Unchanged
- Symbol(GHS)
- 2 · GHS02,GHS06,GHS08
- Signal word
- Danger
- Hazard statements
- 225 · H225-H301+H311+H331-H370
- Precautionary statements
- 210 · P210-P260-P280-P301+P310-P311
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36-37/39
- RIDADR
- 1230 · UN1230 - class 3 - PG 2 - Methanol, solution
- WGK Germany
- 2 · 2
- RTECS
- 5562500 · JM5562500
- HS Code
- 29339900 · 29339900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazardous Substances Data
- 129618 · 129618-40-2(Hazardous Substances Data)
Safety & regulation
Safety data
- wgk
- 2
- rtecs
- JM5562500
- ridadr
- UN1230 - class 3 - PG 2 - Methanol, solution
- hs_code
- 29339900
- risk_code
- 36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS06,GHS08
- hazard_code
- Xi
- safety_code
- 26-36-37/39
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H225-H301+H311+H331-H370
- Precautionary statements
- P210-P260-P280-P301+P310-P311
- Hazardous Substances Data
- 129618-40-2(Hazardous Substances Data)
Chemistry & industry
Applications
DescriptionNevirapine and its analogues exhibit antiretroviral effect against azothymidine-resistant HIV strains. Nevirapine in combination with ZDV and ddI produced approximately 18% higher CD4 cell counts and a decrease in viral load compared with patients who took ZDV and ddI. Nevirapine is recommended with nucleosides for patients infected with HIV-1 who have experienced clinical or immunologic deterioration. The significant side effects of nevirapine are liver dysfunction and skin rashes.
Usesamyloidosis therapy
UsesLabelled Nevirapine , a potent (IC50=84nM) and selective non-nucleoside inhibitor of HIV-1 reverse transcriptase. Antiviral.;Labeled Nevirapine, intended for use as an internal standard for the quantification of Nevirapine by GC- or LC-mass spectrometry.
UsesA potent (IC50=84nM) and selective non-nucleoside inhibitorf HIV-1 reverse transcriptase
General DescriptionNevirapine (Viramune) is more than 90% absorbed by theoral route and is widely distributed throughout the body. Itdistributes well into breast milk and crosses the placenta.Transplacental concentrations are about 50% those ofserum. The drug is extensively transformed by cytochromeP450 (CYP) to inactive hydroxylated metabolites; it mayundergo enterohepatic recycling.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: A dipyridodiazepine that is 5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine which is substituted by methyl, oxo, and cyclopropyl groups at positions 4, 6, and 11, respectively. A non-nucleoside reverse tr nscriptase inhibitor with activity against HIV-1, it is used in combination with other antiretrovirals for the treatment of HIV infection.
Related reactions
Linked notes
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