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Substance Name: Nifedipine [USAN:USP:INN:BAN:JAN]
RN: 21829-25-4
UNII: I9ZF7L6G2L
InChIKey: HYIMSNHJOBLJNT-UHFFFAOYSA-N

Note

  • A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.

Molecular Formula

  • C17-H18-N2-O6

Molecular Weight

  • 346.3372
 

Classification Codes

  • Calcium Channel Blockers
  • Calcium-Regulating Hormones and Agents
  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Membrane Transport Modulators
  • Reproductive Control Agents
  • Reproductive Effect
  • Tocolytic Agents
  • Vasodilator (Coronary)
  • Vasodilator Agents

Names and Synonyms

Name of Substance

  • Nifedipine
  • Nifedipine [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Nifedipine

Synonyms

  • 1,4-Dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic acid dimethyl ester
  • 4-(2'-Nitrophenyl)-2,6-dimethyl-1,4-dihydropyridin-3,5-dicarbonsaeuredimethylester
  • 4-(2'-Nitrophenyl)-2,6-dimethyl-1,4-dihydropyridin-3,5-dicarbonsaeuredimethylester [German]
  • 4-(2'-Nitrophenyl)-2,6-dimethyl-3,5-dicarbomethoxy-1,4-dihydropyridine
  • 5-22-04-00268 (Beilstein Handbook Reference)
  • Adalat
  • Adalat CC
  • Adipine XL
  • Afeditab
  • Afeditab CR
  • BAY A 1040
  • BAYA1040
  • BRN 0497773
  • CCRIS 6074
  • Citilat
  • Cordipin
  • Corinfar
  • Dimethyl 1,4-dihydro-2,6-dimethyl-4-(2'-nitrophenyl)-3,5-pyridinedicarboxylate
  • Dimethyl 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate
  • Dimethyl 1,4-dihydro-2,6-dimethyl-4-(o-nitrophenyl)-3,5-pyridinedicarboxylate
  • EINECS 244-598-3
  • Fenihidin
  • Fenihidine
  • HSDB 7775
  • Nifediac
  • Nifedical
  • Nifedical XL
  • Nifedipine
  • Nifedipino
  • Nifedipino [INN-Spanish]
  • Nifedipinum
  • Nifedipinum [INN-Latin]
  • Oxcord
  • Procardia
  • Procardia XL
  • UNII-I9ZF7L6G2L

Systematic Names

  • 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, dimethyl ester
  • Nifedipine

Superlist Name

  • Nifedipine

Registry Numbers

CAS Registry Number

  • 21829-25-4

FDA UNII

  • I9ZF7L6G2L

Other Registry Numbers

  • 101539-70-2
  • 101554-38-5

Related Registry Number

  • 60299-11-8 (mono-hydrochloride)

System Generated Number

  • 0021829254

Structure Descriptors

InChI

InChI=1S/C17H18N2O6/c1-9-13(16(20)24-3)15(14(10(2)18-9)17(21)25-4)11-7-5-6-8-12(11)19(22)23/h5-8,15,18H,1-4H3

InChIKey

HYIMSNHJOBLJNT-UHFFFAOYSA-N

Smiles

COC(=O)C1=C(C)NC(=C(C1c2ccccc2[N+](=O)[O-])C(=O)OC)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral 100mg/kg (100mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION		 Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1, 1972.
cat LDLo intravenous 500ug/kg (0.5mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION		 Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1, 1972.
child TDLo oral 70mg/kg (70mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION

ENDOCRINE: HYPERGLYCEMIA		 Pediatrics. Vol. 86, Pg. 91, 1990.
man TDLo oral 143ug/kg (0.143mg/kg)   Archives of Internal Medicine. Vol. 158, Pg. 1379, 1998.
man TDLo oral 143ug/kg/1D (0.143mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 380, 1972.
man TDLo oral 714ug/kg (0.714mg/kg) CARDIAC: CHANGE IN RATE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION		 Annals of Emergency Medicine. Vol. 22, Pg. 196, 1993.
man TDLo oral 1143ug/kg/2D- (1.143mg/kg) BEHAVIORAL: TOXIC PSYCHOSIS

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"		 American Journal of Medicine. Vol. 81, Pg. 705, 1986.
man TDLo oral 8571ug/kg (8.571mg/kg) CARDIAC: CHANGE IN RATE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION		 Human & Experimental Toxicology. Vol. 9, Pg. 309, 1990.
man TDLo oral 34286ug/kg (34.286mg/kg) GASTROINTESTINAL: NECROTIC GHANGES

GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Journal of Toxicology, Clinical Toxicology. Vol. 33, Pg. 725, 1995.
man TDLo oral 105mg/kg/26W- (105mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION Lancet. Vol. 339, Pg. 1382, 1992.
mouse LD50 intraperitoneal 185mg/kg (185mg/kg) VASCULAR: REGIONAL OR GENERAL ARTERIOLAR OR VENOUS DILATION

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION		 Pharmaceutical Chemistry Journal Vol. 16, Pg. 817, 1982.
mouse LD50 intravenous 4200ug/kg (4.2mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION		 Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1, 1972.
mouse LD50 oral 202mg/kg (202mg/kg)   United States Patent Document. Vol. #3644627,
mouse LD50 subcutaneous > 10gm/kg (10000mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Kiso to Rinsho. Clinical Report. Vol. 5, Pg. 1831, 1971.
rabbit LD50 intravenous 2mg/kg (2mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION		 Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1, 1972.
rabbit LD50 oral 504mg/kg (504mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Arzneimittel-Forschung. Drug Research. Vol. 35, Pg. 915, 1985.
rat LD50 intraperitoneal 230mg/kg (230mg/kg)   Yakkyoku. Pharmacy. Vol. 28, Pg. 1451, 1977.
rat LD50 intravenous 6mg/kg (6mg/kg)   Archives of Toxicology. Vol. 54, Pg. 275, 1983.
rat LD50 oral 1022mg/kg (1022mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)		 Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1, 1972.
rat LD50 subcutaneous > 10gm/kg (10000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Kiso to Rinsho. Clinical Report. Vol. 5, Pg. 1831, 1971.
women TDLo oral 600ug/kg/45M- (0.6mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION		 Archives of Internal Medicine. Vol. 147, Pg. 556, 1987.
women TDLo oral 800ug/kg/1D-I (0.8mg/kg) BRAIN AND COVERINGS: "CHANGES IN CIRCULATION (HEMORRHAGE, THROMBOSIS, ETC.)"

BEHAVIORAL: HEADACHE

GASTROINTESTINAL: NAUSEA OR VOMITING		 Postgraduate Medical Journal. Vol. 62, Pg. 1029, 1986.
women TDLo oral 2400ug/kg/3D- (2.4mg/kg) BEHAVIORAL: TOXIC PSYCHOSIS British Medical Journal. Vol. 304, Pg. 1225, 1992.
women TDLo oral 11200ug/kg (11.2mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION		 Japanese Journal of Toxicology. Vol. 5, Pg. 79, 1992.
women TDLo oral 31mg/kg/11W-I (31mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 American Heart Journal. Vol. 108, Pg. 611, 1984.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 172-174 deg C   EXP
log P (octanol-water) 2.2 (none)   EXP
Water Solubility 56.3 mg/L 25 EST
Vapor Pressure 2.34E-08 mm Hg 25 EST
Henry's Law Constant 7.31E-14 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.12E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.