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Chemistry

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Also known as: 232925-18-7, 2zrz4tsw3f, Methyl (2s)-2-[[[(2r,3s,5r)-5-[5-[(e)-2-bromoethenyl]-2,4-dioxopyrimidin-1-yl]-3-hydroxyoxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate, Nb-1011, L-alanine, n-(5-((1e)-2-bromoethenyl)-2'-deoxy-p-phenyl-5'-uridylyl)-, methyl ester, Bvdu prodrug
Molecular Formula
C21H25BrN3O9P
Molecular Weight
574.3  g/mol
InChI Key
CFBLUORPOFELCE-BACVZHSASA-N
FDA UNII
2ZRZ4TSW3F

Thymectacin
Brivudine Phosphoramidate is a small molecule phosphoramidate derivative of (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVdU) with potential antineoplastic activity. Selectively active against tumor cells expressing high levels of thymidylate synthase (TS), brivudine is converted intracellularly by TS to bromovinyldeoxyuridine monophosphate (BVdUMP) which competes with the natural substrate, deoxyuridine monophosphate, for binding to TS. Unlike TS inhibitors, this agent is a reversible substrate for TS catalysis. Thus, TS retains activity and converts BVdUMP into cytotoxic metabolites. As key enzyme in the de novo synthesis of dTMP, TS is an enzyme critical to DNA biosynthesis and is overexpressed in many solid tumors.
1 2D Structure

Thymectacin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
methyl (2S)-2-[[[(2R,3S,5R)-5-[5-[(E)-2-bromoethenyl]-2,4-dioxopyrimidin-1-yl]-3-hydroxyoxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate
2.1.2 InChI
InChI=1S/C21H25BrN3O9P/c1-13(20(28)31-2)24-35(30,34-15-6-4-3-5-7-15)32-12-17-16(26)10-18(33-17)25-11-14(8-9-22)19(27)23-21(25)29/h3-9,11,13,16-18,26H,10,12H2,1-2H3,(H,24,30)(H,23,27,29)/b9-8+/t13-,16-,17+,18+,35?/m0/s1
2.1.3 InChI Key
CFBLUORPOFELCE-BACVZHSASA-N
2.1.4 Canonical SMILES
CC(C(=O)OC)NP(=O)(OCC1C(CC(O1)N2C=C(C(=O)NC2=O)C=CBr)O)OC3=CC=CC=C3
2.1.5 Isomeric SMILES
C[C@@H](C(=O)OC)NP(=O)(OC[C@@H]1[C@H](C[C@@H](O1)N2C=C(C(=O)NC2=O)/C=C/Br)O)OC3=CC=CC=C3
2.2 Other Identifiers
2.2.1 UNII
2ZRZ4TSW3F
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 232925-18-7

2. 2zrz4tsw3f

3. Methyl (2s)-2-[[[(2r,3s,5r)-5-[5-[(e)-2-bromoethenyl]-2,4-dioxopyrimidin-1-yl]-3-hydroxyoxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate

4. Nb-1011

5. L-alanine, N-(5-((1e)-2-bromoethenyl)-2'-deoxy-p-phenyl-5'-uridylyl)-, Methyl Ester

6. Bvdu Prodrug

7. (2s)-methyl 2-(((((2r,3s,5r)-5-(5-((e)-2-bromovinyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

8. Brivudine Phosphoramidate

9. Unii-2zrz4tsw3f

10. Schembl13904642

11. Dtxsid00177862

12. 5-(2-bromovinyl)-2'-deoxy-5'-uridyl-phenyl-alanylphosphoramidate, Trans-

13. Db05116

14. (e)-5-(2-bromovinyl)-2'-deoxy-5'-uridyl Phenyl L-methoxyalaninylphosphoramidate

15. E-5-(2-bromovinyl)-2'-deoxyuridine-5'-(l-methylalaninyl)-phenylphosphoramidate

16. Hy-106168

17. Cs-0025066

18. J3.616.614b

19. Q7799611

20. (s)-2-({(2r,3s,5r)-5-[5-((e)-2-bromo-vinyl)-2,4-dioxo-3,4-dihydro-2h-pyrimidin-1-yl]-3-hydroxy-tetrahydro-furan-2-ylmethoxy}-phenoxy-phosphorylamino)-propionic Acid Methyl Ester

21. Methyl (2s)-2-[[[(2r,3s,5r)-5-[5-[(e)-2-bromovinyl]-2,4-dioxo-pyrimidin-1-yl]-3-hydroxy-tetrahydrofuran-2-yl]methoxy-phenoxy-phosphoryl]amino]propanoate

2.4 Create Date
2006-04-28
3 Chemical and Physical Properties
Molecular Weight 574.3 g/mol
Molecular Formula C21H25BrN3O9P
XLogP31.1
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count10
Rotatable Bond Count11
Exact Mass573.05118 g/mol
Monoisotopic Mass573.05118 g/mol
Topological Polar Surface Area153 Ų
Heavy Atom Count35
Formal Charge0
Complexity909
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Investigated for use/treatment in colorectal cancer.


5 Pharmacology and Biochemistry
5.1 Mechanism of Action

NB1011 targets thymidylate synthase (TS), which catalyzes the transformation of E-5-(2-bromovinyl)-2'-deoxyuridine-5'-monophosphate (BVdUMP) into cytotoxic reaction products. Due to the elevated levels of TS expression in tumor cells compared to normal cells, these cytotoxic products are preferentially generated inside tumor cells, and, as expected, NB1011 is more toxic to cells with higher levels of TS expression. Therefore, NB1011 therapy should kill tumor cells without severely damaging normal cells.


ABOUT THIS PAGE

Thymectacin Manufacturers

A Thymectacin manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Thymectacin, including repackagers and relabelers. The FDA regulates Thymectacin manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Thymectacin API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Thymectacin Suppliers

A Thymectacin supplier is an individual or a company that provides Thymectacin active pharmaceutical ingredient (API) or Thymectacin finished formulations upon request. The Thymectacin suppliers may include Thymectacin API manufacturers, exporters, distributors and traders.

Thymectacin GMP

Thymectacin Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Thymectacin GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Thymectacin GMP manufacturer or Thymectacin GMP API supplier for your needs.

Thymectacin CoA

A Thymectacin CoA (Certificate of Analysis) is a formal document that attests to Thymectacin's compliance with Thymectacin specifications and serves as a tool for batch-level quality control.

Thymectacin CoA mostly includes findings from lab analyses of a specific batch. For each Thymectacin CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Thymectacin may be tested according to a variety of international standards, such as European Pharmacopoeia (Thymectacin EP), Thymectacin JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Thymectacin USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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