(6R)-5,6,7,8-Tetrahydro-L-biopterin dihydrochloride

Modify Date: 2024-01-04 09:57:59

(6R)-5,6,7,8-Tetrahydro-L-biopterin dihydrochloride Structure
(6R)-5,6,7,8-Tetrahydro-L-biopterin dihydrochloride structure
 Common Name (6R)-5,6,7,8-Tetrahydro-L-biopterin dihydrochloride
CAS Number 69056-38-8 Molecular Weight 314.17
Density 1.9±0.1 g/cm3 Boiling Point 506.6±60.0 °C at 760 mmHg
Molecular Formula C9H17Cl2N5O3 Melting Point N/A
MSDS Chinese USA Flash Point 260.2±32.9 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of (6R)-5,6,7,8-Tetrahydro-L-biopterin dihydrochloride


Sapropterin dihydrochloride is a synthetic form of BH4 that is approved for the treatment of BH4 responsive PKU. (1) Sapropterin dihydrochloride can stimulate TH and TPH activities leading to improved dopamine and serotonin synthesis despite persistently elevated brain phenylalanine.(2) Sapropterin dihydrochloride is used to lower blood phenylalanine levels in tetrahydrobiopterin-responsive phenylketonuria in conjunction with a phenylalanine-restricted diet.

 Names

Name sapropterin dihydrochloride
Synonym More Synonyms

  Biological Activity

Description Sapropterin dihydrochloride is a synthetic form of BH4 that is approved for the treatment of BH4 responsive PKU. (1) Sapropterin dihydrochloride can stimulate TH and TPH activities leading to improved dopamine and serotonin synthesis despite persistently elevated brain phenylalanine.(2) Sapropterin dihydrochloride is used to lower blood phenylalanine levels in tetrahydrobiopterin-responsive phenylketonuria in conjunction with a phenylalanine-restricted diet.
Related Catalog
References

[1]. Winn SR et al. High dose sapropterin dihydrochloride therapy improves monoamine neurotransmitter turnover in murine phenylketonuria (PKU). Mol Genet Metab. 2016 Jan;117(1):5-11.

[2]. Somaraju UR et al. Sapropterin dihydrochloride for phenylketonuria. Cochrane Database Syst Rev. 2015 Mar 27

[3]. Jurecki ER et al. Sapropterin Dihydrochloride Mixed With Common Foods and Beverages. Top Clin Nutr. 2014 Oct;29(4):325-331.

[4]. Grange DK et al. Sapropterin dihydrochloride use in pregnant women with phenylketonuria: an interim report of the PKU MOMS sub-registry. Mol Genet Metab. 2014 May;112(1):9-16

 Chemical & Physical Properties

Density 1.9±0.1 g/cm3
Boiling Point 506.6±60.0 °C at 760 mmHg
Molecular Formula C9H17Cl2N5O3
Molecular Weight 314.17
Flash Point 260.2±32.9 °C
PSA 136.29000
LogP -4.22
Vapour Pressure 0.0±3.0 mmHg at 25°C
Index of Refraction 1.822
Storage condition −20°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UO3516500
CHEMICAL NAME :
4(1H)-Pteridinone, 5,6,7,8-tetrahydro-2-amino-6-(1,2-dihydroxypropyl)-, dihydrochloride, (6R-(6R*(1R*,2S*)))-
CAS REGISTRY NUMBER :
69056-38-8
LAST UPDATED :
199603
DATA ITEMS CITED :
6
MOLECULAR FORMULA :
C9-H15-N5-O3.2Cl-H
MOLECULAR WEIGHT :
314.21

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 :
1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 43,1191,1992
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1084 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 43,1191,1992
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
150 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 43,1191,1992
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 43,1191,1992
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
239 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 43,1191,1992
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
150 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 43,1191,1992

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Hazard Codes Xn
Risk Phrases R22
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS UO3516500
HS Code 2933990090

 Synthetic Route

6-Biopterin structure

6-Biopterin

CAS#:22150-76-1

~%

(6R)-5,6,7,8-Tetrahydro-L-biopterin dihydrochloride Structure

(6R)-5,6,7,8-Te...

CAS#:69056-38-8

(6R)-5,6,7,8-Tetrahydro-L-biopterin dihydrochloride Structure

(6R)-5,6,7,8-Te...

CAS#:69056-38-8

Literature: Australian Journal of Chemistry, , vol. 35, # 4 p. 785 - 793

 Precursor & DownStream

Precursor  1

DownStream  0

 Customs

HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

 Articles7

More Articles
Tetrahydrobiopterin and cytokines.

Proc. Soc. Exp. Biol. Med. 203 , 1, (1993)

Biosynthesis of tetrahydrobiopterin starts from guanosine triphosphate by the action of guanosine triphosphate cyclohydrolase I, which yields the first intermediate, 7,8-dihydroneopterin triphosphate....

Intravenous treatment of experimental Parkinson's disease in the mouse with an IgG-GDNF fusion protein that penetrates the blood-brain barrier.

Brain Res. 1352 , 208-13, (2010)

Glial-derived neurotrophic factor (GDNF) is a trophic factor for the nigra-striatal tract in experimental Parkinson's disease (PD). The neurotrophin must be administered by intra-cerebral injection, b...

A new resorufin-based alpha-glucosidase assay for high-throughput screening.

Anal. Biochem. 390 , 79-84, (2009)

Mutations in alpha-glucosidase cause accumulation of glycogen in lysosomes, resulting in Pompe disease, a lysosomal storage disorder. Small molecule chaperones that bind to enzyme proteins and correct...

 Synonyms

(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydropteridin-4(1H)-one dihydrochloride
(6R,1'R,2'S)-6-(1',2'-dihydroxypropyl)-5,6,7,8-tetrahydrobiopterin
Dapropterin
(6R)-2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-4(1H)-pteridinone
(6R)-5,6,7,8-tetrahydro-L-biopterin
(6R)-Tetrahydrobiopterin
6R-tetahydrobiopterin
Dapropterin dihydrochloride
Biopten
(6R)-5,6,7,8-TETRAHYDRO-L-BIOPTERIN DIHYDROCHLORIDE
4(1H)-Pteridinone, 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-, (6R)-, hydrochloride (1:2)
sapropterinum
(6R)-2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydropteridin-4(1H)-one
R-THBP
MFCD00891665
(R)-2-Amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydropteridin-4(3H)-one dihydrochloride
(6R)-5,6,7,8-Tetrahydrobiopterin
(6R)-tetrahydrobiopterin dihydrochloride
4(1H)-Pteridinone, 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-, (6R)-
[6R-[6R*(1R*,2S*)]]-2-amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(1H)-pteridinone
(6R)-Tetrahydrobiopterin hydrochloride
(6R)-2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-4(1H)-pteridinone dihydrochloride
Sapropterin
kuvan
(6R)-5,6,7,8-Tetrahydrobiopterin dihydrochloride
6b-5,6,7,8-Tetrahydro-L-biopterin
(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-1H-pteridin-4-one,dihydrochloride
6R-Tetrahydro-L-biopterin
(6R-(6R*(1R*,2S*)))-5,6,7,8-Tetrahydro-2-amino-6-(1,2-dihydroxypropyl)-4(1H)-pteridinone dihydrochloride
R-THBP6R-BH4
(6R)-L-erythro-5,6,7,8-Tetrahydrobiopterin
sapropterina
(6R)-L-erythro-Tetrahydrobiopterin
4(1H)-pteridinone, 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-, (6R)-, dihydrochloride
Sapropterin dihydrochloride
Sapropterin (dihydrochloride)
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