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Chemistry

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Also known as: 27761-19-9, Cysteamine (bitartrate), Mercamine bitartrate, Chebi:50386, Rp-103, Schembl49513
Molecular Formula
C6H13NO6S
Molecular Weight
227.24  g/mol
InChI Key
NSKJTUFFDRENDM-UHFFFAOYSA-N

Cysteamine Bitartrate
A mercaptoethylamine compound that is endogenously derived from the COENZYME A degradative pathway. The fact that cysteamine is readily transported into LYSOSOMES where it reacts with CYSTINE to form cysteine-cysteamine disulfide and CYSTEINE has led to its use in CYSTINE DEPLETING AGENTS for the treatment of CYSTINOSIS.
1 2D Structure

Cysteamine Bitartrate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-aminoethanethiol;2,3-dihydroxybutanedioic acid
2.1.2 InChI
InChI=1S/C4H6O6.C2H7NS/c5-1(3(7)8)2(6)4(9)10;3-1-2-4/h1-2,5-6H,(H,7,8)(H,9,10);4H,1-3H2
2.1.3 InChI Key
NSKJTUFFDRENDM-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(CS)N.C(C(C(=O)O)O)(C(=O)O)O
2.2 Synonyms
2.2.1 MeSH Synonyms

1. 2 Aminoethanethiol

2. 2-aminoethanethiol

3. 35s-labeled Cysteamine

4. Becaptan

5. Beta Mercaptoethylamine

6. Beta-mercaptoethylamine

7. Bitartrate, Cysteamine

8. Cystagon

9. Cysteamine

10. Cysteamine Dihydrochloride

11. Cysteamine Hydrobromide

12. Cysteamine Hydrochloride

13. Cysteamine Maleate (1:1)

14. Cysteamine Tartrate

15. Cysteamine Tartrate (1:1)

16. Cysteamine Tosylate

17. Cysteamine, 35s Labeled

18. Cysteamine, 35s-labeled

19. Cysteinamine

20. Dihydrochloride, Cysteamine

21. Hydrobromide, Cysteamine

22. Hydrochloride, Cysteamine

23. Mercamine

24. Mercaptamine

25. Mercaptoethylamine

26. Tartrate, Cysteamine

27. Tosylate, Cysteamine

2.2.2 Depositor-Supplied Synonyms

1. 27761-19-9

2. Cysteamine (bitartrate)

3. Mercamine Bitartrate

4. Chebi:50386

5. Rp-103

6. Schembl49513

7. Chembl2062263

8. Bcp15048

9. Akos024332936

10. 2-aminoethanethiol 2,3-dihydroxysuccinate

11. Db-114321

12. Ft-0696891

13. 2-aminoethanethiol;2,3-dihydroxybutanedioic Acid

14. A900934

15. Q27122045

2.2.3 Other Synonyms

1. Cysteamine (usan)

2. Mecramine

2.3 Create Date
2007-12-05
3 Chemical and Physical Properties
Molecular Weight 227.24 g/mol
Molecular Formula C6H13NO6S
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count8
Rotatable Bond Count4
Exact Mass227.04635831 g/mol
Monoisotopic Mass227.04635831 g/mol
Topological Polar Surface Area142 Ų
Heavy Atom Count14
Formal Charge0
Complexity144
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count2
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Cystine Depleting Agents

Compounds and drugs that react with CYSTINE and convert it into a compound that can be more easily metabolized or intracellularly transported. Drugs in this class have been used to treat CYSTINOSIS. (See all compounds classified as Cystine Depleting Agents.)


4.2 FDA Pharmacological Classification
4.2.1 Pharmacological Classes
Cystine Disulfide Reduction [MoA]; Cystine Depleting Agent [EPC]

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18-Jan-2021
08-Oct-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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DOSAGE - CAPSULE, DELAYED RELEASE;ORAL - EQ 2...DOSAGE - CAPSULE, DELAYED RELEASE;ORAL - EQ 25MG BASE

USFDA APPLICATION NUMBER - 203389

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DOSAGE - CAPSULE, DELAYED RELEASE;ORAL - EQ 7...DOSAGE - CAPSULE, DELAYED RELEASE;ORAL - EQ 75MG BASE

USFDA APPLICATION NUMBER - 203389

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