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Substance Name: Nafronyl oxalate [USAN]
RN: 3200-06-4
UNII: 5ADB8D9388
InChIKey: SSAJNPNVUYMUCI-UHFFFAOYSA-N

Note

  • A drug used in the management of peripheral and cerebral vascular disorders. It is claimed to enhance cellular oxidative capacity and to be a spasmolytic. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1310) It may also be an antagonist at 5HT-2 serotonin receptors.

Molecular Formula

  • C24-H33-N-O3.C2-H2-O4

Molecular Weight

  • 473.562
 

Classification Codes

  • Drug / Therapeutic Agent
  • Reproductive Effect
  • Vasodilator
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Names and Synonyms

Name of Substance

  • Nafronyl acid oxalate
  • Nafronyl oxalate [USAN]

Synonyms

  • 2-(Diethylamino)ethyl tetrahydro-alpha-(1-naphthylmethyl)-2-furanpropionate oxalate (1:1)
  • Dubimax
  • Dusodril
  • EINECS 221-703-0
  • EU-1806
  • Gevatran
  • Iridus
  • LS 121
  • LS-121
  • Nafronyl oxalate
  • Naftidrofuryl oxalate
  • Naphtidrofuryl oxalate
  • NSC 225233
  • Praxilene
  • UNII-5ADB8D9388

Systematic Names

  • 2-Furanpropanoic acid, tetrahydro-alpha-(1-naphthalenylmethyl)-, 2-(diethylamino)ethyl ester, ethanedioate (1:1)
  • 2-Furanpropionic acid, tetrahydro-alpha-(1-naphthylmethyl)-, 2-(diethylamino)ethyl ester, oxalate (1:1)
  • Diethyl(2-(2-(1-naphthylmethyl)-3-(tetrahydro-2-furyl)propionyloxy)ethyl)ammonium hydrogen oxalate

Registry Numbers

CAS Registry Number

  • 3200-06-4

FDA UNII

  • 5ADB8D9388

Other Registry Number

  • 26263-44-5

System Generated Number

  • 0003200064

Molecular Formulas

Molecular Formula

  • C24-H33-N-O3.C2-H2-O4

Molecular Formula Fragments

  • C2-H2-O4
  • C24-H33-N-O3
  • COMPONENT

Structure Descriptors

InChI

1S/C24H33NO3.C2H2O4/c1-3-25(4-2)14-16-28-24(26)21(18-22-12-8-15-27-22)17-20-11-7-10-19-9-5-6-13-23(19)20;3-1(4)2(5)6/h5-7,9-11,13,21-22H,3-4,8,12,14-18H2,1-2H3;(H,3,4)(H,5,6)

InChIKey

SSAJNPNVUYMUCI-UHFFFAOYSA-N

Smiles

c12c(C[C@@H](C[C@@H]3CCCO3)C(OCC[NH+](CC)CC)=O)cccc1cccc2.C(C(=O)[O-])(O)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 71mg/kg (71mg/kg)   Chimica Therapeutica. Vol. 3, Pg. 463, 1968.
mouse LD50 intramuscular 696mg/kg (696mg/kg)   Chimica Therapeutica. Vol. 3, Pg. 463, 1968.
mouse LD50 intraperitoneal 159mg/kg (159mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 14, Pg. 1237, 1986.
mouse LD50 intravenous 18400ug/kg (18.4mg/kg)   United States Patent Document. Vol. #4439442,
mouse LD50 oral 365mg/kg (365mg/kg)   United States Patent Document. Vol. #4652583,
mouse LD50 subcutaneous 547mg/kg (547mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 14, Pg. 1237, 1986.
rabbit LDLo intravenous 8mg/kg (8mg/kg) AUTONOMIC NERVOUS SYSTEM: "SMOOTH MUSCLE RELAXANT (MECHANISM UNDEFINED, SPASMOLYTIC)"

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. Vol. 11, Pg. 103, 1985.
rabbit LDLo oral 1gm/kg (1000mg/kg) GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. Vol. 11, Pg. 81, 1985.
rat LD50 intraperitoneal 98mg/kg (98mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 14, Pg. 1237, 1986.
rat LD50 intravenous 11080ug/kg (11.08mg/kg)   United States Patent Document. Vol. #4439442,
rat LD50 oral 711mg/kg (711mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 14, Pg. 1237, 1986.
rat LD50 subcutaneous 896mg/kg (896mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 14, Pg. 1237, 1986.