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Substance Name: Droxidopa [USAN:INN:JAN]
RN: 23651-95-8
UNII: J7A92W69L7
InChIKey: QXWYKJLNLSIPIN-JGVFFNPUSA-N

Note

  • A precursor of noradrenaline that is used in the treatment of parkinsonism. The racemic form (DL-threo-3,4-dihydroxyphenylserine) has also been used, and has been investigated in the treatment of orthostatic hypotension. There is a deficit of noradrenaline as well as of dopamine in Parkinson's disease and it has been proposed that this underlies the sudden transient freezing seen usually in advanced disease. Administration of DL-threo-3,4-dihydroxyphenylserine has been claimed to result in an improvement in this phenomenon but controlled studies have failed to demonstrate improvement. (Reynolds JEF(Ed): Martindale: The Extra Pharmacopoeia (electronic version). Micromedex, Inc, Englewood, CO, 1995)

Molecular Formula

  • C9-H11-N-O5

Molecular Weight

  • 213.1879
 

Classification Codes

  • Anti-Dyskinesia Agents
  • Antiparkinson Agents
  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Neurogenic Hypotension
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Droxidopa
  • Droxidopa [USAN:INN:JAN]

MeSH Heading

  • Droxidopa

Synonyms

  • (-)-(2S,3R)-2-Amino-3-hydroxy-3-(3,4-dihydroxyphenyl)propionic acid
  • DOPS
  • Droxidopa
  • Droxidopa [Latin]
  • L-DOPS
  • L-threo-3-(3,4-Dihydroxyphenyl)serine
  • L-Threodops
  • L-Tyrosine, beta,3-dihydroxy-, threo-
  • Norethra
  • Northera
  • SM 5688
  • threo-Dopaserine
  • UNII-J7A92W69L7

Systematic Names

  • (-)-threo-3-(3,4-Dihydroxyphenyl)-L-serine
  • L-Tyrosine, beta,3-dihydroxy-, (beta-R)- (9CI)
  • L-Tyrosine, beta,3-dihydroxy-, threo-
  • Serine, 3-(3,4-dihydroxyphenyl)-, L-threo-

Registry Numbers

CAS Registry Number

  • 23651-95-8

FDA UNII

  • J7A92W69L7

System Generated Number

  • 0023651958

Structure Descriptors

InChI

InChI=1S/C9H11NO5/c10-7(9(14)15)8(13)4-1-2-5(11)6(12)3-4/h1-3,7-8,11-13H,10H2,(H,14,15)/t7-,8+/m0/s1

InChIKey

QXWYKJLNLSIPIN-JGVFFNPUSA-N

Smiles

N[C@@H]([C@H](O)c1ccc(O)c(O)c1)C(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 5gm/kg (5000mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

CARDIAC: OTHER CHANGES
Yakkyoku. Pharmacy. Vol. 40, Pg. 1935, 1989.
monkey LD50 oral > 5gm/kg (5000mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

CARDIAC: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
Yakkyoku. Pharmacy. Vol. 40, Pg. 1935, 1989.
mouse LD50 intravenous > 100mg/kg (100mg/kg)   Drugs in Japan Vol. -, Pg. 758, 1990.
mouse LD50 oral > 10gm/kg (10000mg/kg)   Drugs in Japan Vol. -, Pg. 758, 1990.
mouse LD50 subcutaneous > 10gm/kg (10000mg/kg)   Drugs in Japan Vol. -, Pg. 758, 1990.
rat LD50 intravenous 16mg/kg (16mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 15(Suppl,
rat LD50 oral > 10gm/kg (10000mg/kg)   Drugs in Japan Vol. -, Pg. 758, 1990.
rat LD50 subcutaneous 84mg/kg (84mg/kg)   Drugs in Japan Vol. -, Pg. 758, 1990.