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50731-20-9 23651-95-8
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23651-95-8

23651-95-8 structure
23651-95-8 structure
  • Name: droxidopa
  • Chemical Name: droxidopa
  • CAS Number: 23651-95-8
  • Molecular Formula: C9H11NO5
  • Molecular Weight: 213.187
  • Catalog: API Circulatory system medication Antihypertensive drug
  • Create Date: 2018-02-05 08:00:00
  • Modify Date: 2024-01-03 09:28:21
  • Droxidopa(L-DOPS, SM5688) is a synthetic amino acid precursor which acts as a prodrug to the neurotransmitters norepinephrine (noradrenaline) and epinephrine (adrenaline); capable of crossing the protective blood–brain barrierIC50 value: Target: The acute administration of droxidopa in PVL and BDL rats caused a significant and maintained increase in arterial pressure and mesenteric arterial resistance, with a significant decrease of mesenteric arterial and portal blood flow, without changing portal pressure and renal blood flow [1]. L-threo-dihydroxyphenyslerine (Droxidopa) is a pro-drug which has a structure similar to noradrenaline, but with a carboxyl group. It has no pressor effects in this form. It can be administered orally, unlike noradrenaline, and after absorption is converted by the enzyme dopa decarboxylase into noradrenaline thus increasing levels of the neurotransmitter which is identical to endogenous noradrenaline [2].
Name droxidopa
Synonyms (-)-(2s,3r)-2-amino-3-hydroxy-3-(3,4-dihydroxyphenyl)propionic acid
DL-DOPS
DL-threo-Dihydroxyphenylserine
L-DOPS
3-dihydroxy-betthreo-dl-tyrosin
(2S,3R)-3-(3,4-Dihydroxyphenyl)-2-amino-3-hydroxypropanoic acid
3-dihydroxy-dl-tyrosinethreo-bet
DROXIDOPA
(2S,3R)-2-Amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropionic Acid
Benzeneethanaminium, α-carboxy-β,3,4-trihydroxy-, inner salt, (αS,βS)-
(2S,3R)-2-Amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid
L-threo-DOPS
DL-THREO-DOPS
L-threo-3,4-Dihydroxyphenylserine
(2S,3S)-2-Ammonio-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoate
Droxidopa L-threo 3,4-Dihydroxyphenylserine
DL-threo-Droxidopa
threo-Dopaserine
L-threo-3-(3,4-Dihydroxyphenyl)serine
Description Droxidopa(L-DOPS, SM5688) is a synthetic amino acid precursor which acts as a prodrug to the neurotransmitters norepinephrine (noradrenaline) and epinephrine (adrenaline); capable of crossing the protective blood–brain barrierIC50 value: Target: The acute administration of droxidopa in PVL and BDL rats caused a significant and maintained increase in arterial pressure and mesenteric arterial resistance, with a significant decrease of mesenteric arterial and portal blood flow, without changing portal pressure and renal blood flow [1]. L-threo-dihydroxyphenyslerine (Droxidopa) is a pro-drug which has a structure similar to noradrenaline, but with a carboxyl group. It has no pressor effects in this form. It can be administered orally, unlike noradrenaline, and after absorption is converted by the enzyme dopa decarboxylase into noradrenaline thus increasing levels of the neurotransmitter which is identical to endogenous noradrenaline [2].
Related Catalog
References

[1]. Coll M, et al. Droxidopa, an oral norepinephrine precursor, improves hemodynamic and renal alterations of portal hypertensive rats. Hepatology. 2012 Nov;56(5):1849-60.

[2]. Mathias CJ. L-dihydroxyphenylserine (Droxidopa) in the treatment of orthostatic hypotension: the European experience. Clin Auton Res. 2008 Mar;18 Suppl 1:25-9.
Density 1.608g/cm3
Boiling Point 549.8±50.0 °C at 760 mmHg
Melting Point 232-235° (dec); mp 229-232° (dec) (Ohashi)
Molecular Formula C9H11NO5
Molecular Weight 213.187
Flash Point 286.3±30.1 °C
Exact Mass 213.063721
PSA 124.01000
LogP -0.95
Vapour Pressure 0.0±1.6 mmHg at 25°C
Index of Refraction 1.692
Storage condition 2-8C

CHEMICAL IDENTIFICATION

RTECS NUMBER :
VT9626010
CHEMICAL NAME :
Serine, 3-(3,4-dihydroxyphenyl)-, L-threo-
CAS REGISTRY NUMBER :
23651-95-8
LAST UPDATED :
199603
DATA ITEMS CITED :
12
MOLECULAR FORMULA :
C9-H11-N-O5
MOLECULAR WEIGHT :
213.21

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,758,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
84 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,758,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
16 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - ataxia Lungs, Thorax, or Respiration - other changes
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 15(Suppl 2),257,1987
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,758,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,758,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>100 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,758,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Cardiac - other changes Lungs, Thorax, or Respiration - dyspnea Kidney, Ureter, Bladder - other changes
REFERENCE :
YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 40,1935,1989
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Cardiac - other changes Lungs, Thorax, or Respiration - respiratory depression Kidney, Ureter, Bladder - other changes
REFERENCE :
YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 40,1935,1989 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
13200 mg/kg
SEX/DURATION :
female 15 day(s) pre-mating female 1-7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 15(Suppl 2),283,1987
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
2200 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 15(Suppl 2),283,1987
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1500 mg/kg
SEX/DURATION :
female 17-21 day(s) after conception lactating female 20 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain) Reproductive - Effects on Newborn - physical Reproductive - Effects on Newborn - other postnatal measures or effects
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 15(Suppl 2),283,1987
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
15 gm/kg
SEX/DURATION :
female 17-21 day(s) after conception lactating female 20 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Maternal Effects - parturition
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 15(Suppl 2),283,1987
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
Hazard Codes Xi
Risk Phrases 36/37/38
Safety Phrases 26
RIDADR NONH for all modes of transport
RTECS VT9626010
HS Code 29225090

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