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Substance Name: Promethazine [INN:BAN]
RN: 60-87-7
UNII: FF28EJQ494
InChIKey: PWWVAXIEGOYWEE-UHFFFAOYSA-N

Note

  • A phenothiazine derivative with histamine H1-blocking, antimuscarinic, and sedative properties. It is used as an antiallergic, in pruritus, for motion sickness and sedation, and also in animals.

Molecular Formula

  • C17-H20-N2-S

Molecular Weight

  • 284.425
 

Classification Codes

  • Anti-Allergic Agents
  • Antipruritics
  • Dermatologic Agents
  • Drug / Therapeutic Agent
  • Histamine Agents
  • Histamine Antagonists
  • Histamine H1 Antagonists
  • Human Data
  • Mutation Data
  • Neurotransmitter Agents
  • Reproductive Effect
  • Skin / Eye Irritant

Names and Synonyms

Name of Substance

  • Promethazine
  • Promethazine [INN:BAN]

MeSH Heading

  • Promethazine

Synonyms

  • (2-Dimethylamino-2-methyl)ethyl-N-dibenzoparathiazine
  • 10-(2-(Dimethylamino)-2-methylethyl)phenothiazine
  • 10-(2-(Dimethylamino)propyl)phenothiazine
  • 10H-Phenothiazine-10-ethanamine, N,N,alpha-trimethyl-
  • 3277 RP
  • 4-27-00-01253 (Beilstein Handbook Reference)
  • A-91033
  • Antiallersin
  • Aprobit
  • Atosil
  • Avomine
  • BRN 0088554
  • Camergan
  • CCRIS 7056
  • Dimapp
  • Dimethylamino-isopropyl-phenthiazin
  • Dimethylamino-isopropyl-phenthiazin [German]
  • Diphergan
  • Diprazine
  • Diprozin
  • EINECS 200-489-2
  • Fargan
  • Fenazil
  • Fenetazina
  • Fenetazine
  • Hiberna
  • Histargan
  • HSDB 3173
  • Isophenergan
  • Lilly 01516
  • Lilly 1516
  • Metaryl
  • N,N,alpha-Trimethyl-10H-phenothiazine-10-ethanamine
  • N-(2'-Dimethylamino-2'-methyl)ethylphenothiazine
  • N-Dimethylamino-2-methylethyl thiodiphenylamine
  • NCI-C60673
  • NSC 30321
  • Pelpica
  • Phargan
  • Phenargan
  • Phenerzine
  • Phenoject-50
  • Phenothiazine, 10-(2-dimethylaminopropyl)-
  • Phensedyl
  • Pilothia
  • Pipolphene
  • Pro-50
  • Proazamine
  • Procit
  • Promacot
  • Promazinamide
  • Promergan
  • Promesan
  • Prometazina
  • Prometazina [INN-Spanish]
  • Prometh
  • Promethacon
  • Promethazin
  • Promethazine
  • PromethazineHcl
  • Promethazinum
  • Promethazinum [INN-Latin]
  • Promethegan
  • Promezathine
  • Prorex
  • Protazine
  • Provigan
  • Pyrethiazine
  • RP 3277
  • SKF 1498
  • Tanidil
  • Thiergan
  • UNII-FF28EJQ494
  • Vallergine
  • WY 509

Systematic Names

  • 10H-Phenothiazine-10-ethanamine, N,N,alpha-trimethyl-
  • 10H-Phenothiazine-10-ethanamine, N,N,alpha-trimethyl- (9CI)
  • Phenothiazine, 10-(2-dimethylaminopropyl)-
  • Promethazine

Registry Numbers

CAS Registry Number

  • 60-87-7

FDA UNII

  • FF28EJQ494

Other Registry Number

  • 73745-50-3

System Generated Number

  • 0000060877

Structure Descriptors

InChI

1S/C17H20N2S/c1-13(18(2)3)12-19-14-8-4-6-10-16(14)20-17-11-7-5-9-15(17)19/h4-11,13H,12H2,1-3H3

InChIKey

PWWVAXIEGOYWEE-UHFFFAOYSA-N

Smiles

CC(CN1c2ccccc2Sc3c1cccc3)N(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo oral 250mg/kg (250mg/kg) BEHAVIORAL: ATAXIA

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Kiso to Rinsho. Clinical Report. Vol. 4, Pg. 1772, 1970.
child TDLo skin 13mg/kg (13mg/kg) BEHAVIORAL: WAKEFULNESS

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE
Canadian Medical Association Journal. Vol. 130, Pg. 1460, 1984.
dog LDLo oral 500mg/kg (500mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Kiso to Rinsho. Clinical Report. Vol. 4, Pg. 1772, 1970.
guinea pig LD50 intraperitoneal 116mg/kg (116mg/kg)   Medicina Experimentalis. Vol. 8, Pg. 237, 1963.
guinea pig LD50 intravenous 27mg/kg (27mg/kg)   Pharmazie. Vol. 25, Pg. 91, 1970.
guinea pig LD50 oral 640mg/kg (640mg/kg)   Pharmazie. Vol. 25, Pg. 91, 1970.
guinea pig LD50 subcutaneous 520mg/kg (520mg/kg)   Pharmazie. Vol. 25, Pg. 91, 1970.
man TDLo intravenous 2857ug/kg/C (2.857mg/kg) BEHAVIORAL: COMA Annals of Emergency Medicine. Vol. 24, Pg. 979, 1994.
mouse LD50 intramuscular 175mg/kg (175mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
mouse LD50 intraperitoneal 124mg/kg (124mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Journal of Pharmacology and Experimental Therapeutics. Vol. 108, Pg. 201, 1953.
mouse LD50 intravenous 40mg/kg (40mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
mouse LD50 oral 326mg/kg (326mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 7, Pg. 237, 1957.
mouse LD50 subcutaneous 225mg/kg (225mg/kg)   Produits Pharmaceutiques. Vol. 2, Pg. 53, 1947.
rabbit LD50 intravenous 19mg/kg (19mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 120, Pg. 450, 1959.
rabbit LD50 oral 580mg/kg (580mg/kg)   Pharmazie. Vol. 25, Pg. 91, 1970.
rat LD50 intramuscular 169mg/kg (169mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 intravenous 45mg/kg (45mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 120, Pg. 450, 1959.
rat LD50 subcutaneous 700mg/kg (700mg/kg)   Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 144, Pg. 887, 1950.
rat LD50 subcutaneous 700mg/kg (700mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 144, Pg. 887, 1950.
rat LDLo intraperitoneal 140mg/kg (140mg/kg)   Toxicology and Applied Pharmacology. Vol. 1, Pg. 156, 1959.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 60 deg C   EXP
pKa Dissociation Constant 9.1 (none)   EXP
log P (octanol-water) 4.81 (none)   EXP
Water Solubility 15.6 mg/L 24 EXP
Vapor Pressure 1.37E-06 mm Hg 25 EST
Henry's Law Constant 4.98E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.82E-10 cm3/molecule-sec 25 EST

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