Basic information
- CAS
22668-01-5- Standard SMILES
O=C(Cn1ccnc1[N+](=O)[O-])NCCO- InChIKey
WCDWBPCFGJXFJZ-UHFFFAOYSA-N- Molecular formula
- C7H10N4O4
- Average molar mass
- 214.18 g/mol
- Monoisotopic mass
- 214.07020481
Overview
Etanidazole is a monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2-nitro-1H-imidazol-1-yl)acetic acid with the amino group of ethanolamine. Used as a radiosensitising agent for hypoxic tumour cells. It has a role as a radiosensitizing agent, an alkylating agent, an antineoplastic agent and a prodrug. It is a member of imidazoles, a monocarboxylic acid amide and a C-nitro compound. It is functionally related to an ethanolamine.
Names & identifiers
- Preferred name
- Etanidazole
- IUPAC
- N-(2-hydroxyethyl)-2-(2-nitroimidazol-1-yl)acetamide
- English name
- ETANIDAZOLE
- Molecular formula
- C7H10N4O4
- Molecular weight
- 214.18
Names & synonyms
etanidazole22668-01-5RadinylEtanidazolEtanidazolum1H-Imidazole-1-acetamide, N-(2-hydroxyethyl)-2-nitro-NSC-301467SR 2508SR-2508N-(2-hydroxyethyl)-2-(2-nitro-1H-imidazol-1-yl)acetamideN-(2-Hydroxyethyl)-2-nitro-1H-imidazole-1-acetamideNSC 301467
Show more names
SP-2508Etanidazole (SR-2508)N-(2-Hydroxyethyl)-1H-imidazole-1-acetamiden-(2-hydroxyethyl)-2-nitro-imidazole-1-acetamidn-(2-hydroxyethyl)-2-nitro-1h-imidazole-1-acetamidN-[2-HYDROXYETHYL]-2-NITRO-1H-IMIDAZOLE-1-ACETAMIDE
N-(2-Hydroxyethyl)-2-nitroimidazole-1-acetamide30DKA3Q1HLNSC301467N-(2-Hydroxyethyl)-1-(2-nitro-1-imidazolyl)acetamideCHEBI:75473SR2508RefChem:591350636-578-1
Database identifiers
- CAS
22668-01-5- PubChem CID
- 3276
- DTXSID
DTXSID8045434
Properties
Computed structural properties
- XLogP
- -1.3
- Topological polar surface area
- 113 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 242
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP-1.32
Solubility
Water > 100 (mg/mL)
Methanol 60 (mg/mL)
Ethanol 30 (mg/mL)
Chloroform < 1 (mg/mL)
Stability/Shelf LifeBulk: The sample is stable at room temperature for at least one month (HPLC).
Solution: As a 10% solution in water, the chemical is stable for at least 24 hours (HPLC).
Physicochemical properties
- Melting point
- 162 · 162-163° (Beaman); mp 164.5-165° (Lee)
- Boiling point
- 354.3 °C · 354.3°C (rough estimate)
- Density
- 1.448 · 1.4480 (rough estimate)
- refractive index
- 1.67 · 1.6700 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Acetone (Slightly), Methanol (Slightly)
- form
- Solid
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Toxicology
Toxicity Data
Mouse(ip): LD50: 3300 mg/kg
Mouse(iv): LD50: 4400 mg/kg
Safety data
- wgk
- 3
- rtecs
- NI3355000
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Hazard statements
- H335-H319-H315
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Drugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells.
Applications
UsesAntineoplastic (hypoxic cell radiosensitizer).
UsesEtanidazole is a kind of hypoxic radiosensitizer (a drug that sensitizes tumour cells to radiation therapy). Etanidazole is used in conjunction with Paclitaxel (P132500) to treat glioma, and is also used with Carboplatin (C177500) to treat advanced ovarian cancer.
Upstream & downstream products
Upstream raw materials
Suppliers24 total
艾吉析科技（上海）有限公司17717235263 · [email protected]
杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
江苏艾康生物医药研发有限公司025-66061636 19370895928 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
Related reactions
2 records
Compound notes
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