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Substance Name: Clemastine fumarate [USAN:USP:BAN:JAN]
RN: 14976-57-9
UNII: 19259EGQ3D
InChIKey: PMGQWSIVQFOFOQ-YKVZVUFRSA-N

Note

  • A histamine H1 antagonist used as the hydrogen fumarate in hay fever, rhinitis, allergic skin conditions, and pruritus. It causes drowsiness.

Molecular Formula

  • C21-H26-Cl-N-O.C4-H4-O4

Molecular Weight

  • 459.967
 

Classification Codes

  • Anti-Allergic Agents
  • Antihistaminic
  • Antipruritics
  • Dermatologic Agents
  • Drug / Therapeutic Agent
  • Histamine Agents
  • Histamine Antagonists
  • Histamine H1 Antagonists
  • Neurotransmitter Agents

Names and Synonyms

Name of Substance

  • Clemastine fumarate
  • Clemastine fumarate [USAN:USP:BAN:JAN]

Synonyms

  • (+)-(2R)-2-(2-(((R)-p-Chloro-alpha-methyl-alpha-phenylbenzyl)oxy)ethyl)-1-methylpyrrolidine fumarate (1:1)
  • (+)-2-(2-((p-Chloro-alpha-methyl-alpha-phenylbenzyl)oxy)ethyl)-1-methyl pyrrolidine fumarate
  • Agasten
  • Aloginan
  • Alphamin
  • Anhistan
  • Clemanil
  • Clemastine fumarate
  • Clemastine hydrogen fumarate
  • EINECS 239-055-2
  • Fuluminol
  • HSDB 6507
  • Inbestan
  • Kinotomin
  • Lacretin
  • Lecasol
  • Maikohis
  • Mallermin-F
  • Marsthine
  • Masletine
  • Meclastine hydrogen fumarate
  • Mecloprodine
  • Piloral
  • Pyrrolidine, 2-(2-(1-(4-chlorophenyl)-1-phenylethoxy)ethyl)-1-methyl-, (R-(R*,R*))-, (E)-2-butenedioate (1:1)
  • Reconin
  • Tavegil
  • Tavegyl
  • Tavist
  • Tavist-1
  • Telgin-G
  • Topcare dayhist allergy
  • Trabest
  • UNII-19259EGQ3D
  • Xolamin

Systematic Names

  • (R-(R*,R*))-2-(2-(1-(p-Chlorophenyl)-1-phenylethoxy)ethyl)-1-methylpyrrolidinium hydrogen fumarate
  • Pyrrolidine, 2-(2-((p-chloro-alpha-methyl-alpha-phenylbenzyl)oxy)ethyl)-1-methyl-, (+)-, fumarate (1:1)
  • Pyrrolidine, 2-(2-(1-(4-chlorophenyl)-1-phenylethoxy)ethyl)-1-methyl-, (R-(R*,R*))-, (E)-2-butenedioate (1:1)

Mixture Name

  • Contac 12 Hour Allergy

Registry Numbers

CAS Registry Number

  • 14976-57-9

FDA UNII

  • 19259EGQ3D

System Generated Number

  • 0014976579

Molecular Formulas

Molecular Formula

  • C21-H26-Cl-N-O.C4-H4-O4

Molecular Formula Fragments

  • C21-H26-Cl-N-O
  • C4-H4-O4
  • COMPONENT

Structure Descriptors

InChI

1S/C21H26ClNO.C4H4O4/c1-21(17-7-4-3-5-8-17,18-10-12-19(22)13-11-18)24-16-14-20-9-6-15-23(20)2;5-3(6)1-2-4(7)8/h3-5,7-8,10-13,20H,6,9,14-16H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1+/t20-,21-;/m1./s1

InChIKey

PMGQWSIVQFOFOQ-YKVZVUFRSA-N

Smiles

C[C@@](c1ccccc1)(c2ccc(cc2)Cl)OCC[C@H]3CCCN3C.C(=C/C(=O)O)\C(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous > 50mg/kg (50mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Bollettino Chimico Farmaceutico. Vol. 106, Pg. 467, 1967.
dog LD50 oral 175mg/kg (175mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Bollettino Chimico Farmaceutico. Vol. 106, Pg. 467, 1967.
mouse LD50 intravenous 43mg/kg (43mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Bollettino Chimico Farmaceutico. Vol. 106, Pg. 467, 1967.
mouse LD50 oral 730mg/kg (730mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Bollettino Chimico Farmaceutico. Vol. 106, Pg. 467, 1967.
rabbit LD50 intravenous 19mg/kg (19mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Bollettino Chimico Farmaceutico. Vol. 106, Pg. 467, 1967.
rabbit LD50 oral 1gm/kg (1000mg/kg)   Drugs in Japan Vol. 6, Pg. 230, 1982.
rat LD50 intravenous 82mg/kg (82mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Bollettino Chimico Farmaceutico. Vol. 106, Pg. 467, 1967.
rat LD50 oral 3550mg/kg (3550mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Bollettino Chimico Farmaceutico. Vol. 106, Pg. 467, 1967.