ChemicalBook > CAS DataBase List > N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester

N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester

Product Name: N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester
CAS No.: 918633-87-1
Chemical Name: N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester
Synonyms: TH 302;CS-516;HAP-302;EOS-61724;EVOFOSFAMID;EvofosfaMide;TH-302, >=98%;TH 302; TH302;Evofosfamide(TH 302);TH-302 (Evofosfamide)
CBNumber: CB52604209
Molecular Formula: C9H16Br2N5O4P
Formula Weight: 449.04
MOL File: 918633-87-1.mol

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N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester Property

Melting point:: 97-98°C
Boiling point:: 565.4±60.0 °C(Predicted)
Density: 1.97
storage temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility: DMSO (Slightly), Methanol (Slightly)
pka: 0.34±0.70(Predicted)
form: Solid
color: Off-White to Pale Yellow
InChI: InChI=1S/C9H16Br2N5O4P/c1-15-8(6-12-9(15)16(17)18)7-20-21(19,13-4-2-10)14-5-3-11/h6H,2-5,7H2,1H3,(H2,13,14,19)
InChIKey: UGJWRPJDTDGERK-UHFFFAOYSA-N
SMILES: P(NCCBr)(NCCBr)(OCC1N(C)C([N+]([O-])=O)=NC=1)=O

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 22195
Product name: TH-302
Purity: ≥95%
Packaging: 1mg
Price: $40
Updated: 2024/03/01

Cayman Chemical

Product number: 22195
Product name: TH-302
Purity: ≥95%
Packaging: 5mg
Price: $168
Updated: 2024/03/01

Cayman Chemical

Product number: 22195
Product name: TH-302
Purity: ≥95%
Packaging: 10mg
Price: $276
Updated: 2024/03/01

Cayman Chemical

Product number: 22195
Product name: TH-302
Purity: ≥95%
Packaging: 25mg
Price: $590
Updated: 2024/03/01

TRC

Product number: T338200
Product name: TH-302
Packaging: 5mg
Price: $250
Updated: 2021/12/16

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N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester Chemical Properties,Usage,Production

Description

TH-302 is a hypoxia-activated prodrug and DNA alkylating agent with anticancer activity. It is selectively cytotoxic to H460 human non-small cell lung cancer (NSCLC) cells grown under hypoxic over normoxic conditions (IC₅₀s = 0.019 and 5.1 μM, respectively). Under hypoxic conditions, TH-302 undergoes a one-electron reduction to form an active radical intermediate that is then further reduced to form a DNA-intercalating hydroxylamine. Under normoxic conditions, the radical intermediate is quenched and induces reformation of the inactive nitroazole prodrug. TH-302 reduces survival of H460 and HT-29 cells in a clonogenic assay (IC₅₀s = 0.2 and 0.2 μM, respectively). In vivo, TH-302 (33 mg/kg per day) inhibits primary tumor growth by 41% in an MIA PaCa-2-RFP mouse orthotopic xenograft model. It inhibits tumor growth by greater than 40% in Calu-6 NSCLC, H82 small cell lung, A375 melanoma, PC-3 prostate, and BxPC-3 pancreatic cancer mouse xenograft models when administered at 50 mg/kg.

Uses

TH-302 is a 2-nitroimidazole triggered hypoxia-activated prodrug (HAP) of bromo-isophosphoramide mustard. Studies have shown that TH-302 treatment exhibited hypoxia-selective cytotoxicity and DNA damage in human cancer cell

in vivo

Evofosfamide (TH-302) is a hypoxia-activated prodrug known to activate selectively under the hypoxic conditions commonly found in solid tumors. The mean values of normalized K^trans decrease 69.2% for Evofosfamide (TH-302)-treated mice in Hs766t tumors, decrease 46.1% for Mia PaCa-2 tumors and increase 4.9% in SU.86.86 tumors. Both changes for Hs766t and Mia PaCa-2 treatment groups are statistically significant (P<0.01) when compare to their own control group^[2]. A significant reduction in the hypoxic fraction (HF) to 2.1%±4.7% is seen after 95% oxygen breathing (P<0.001), whereas 7% oxygen breathing significantly increase the HF to 29.5%±14.7% (P=0.029). Exposing rhabdomyosarcoma-bearing rats to increasing oxygen conditions abolish the effect of TH-302 and reduce the T4×SV from 20.4±3.5 to 15.3±2.5 days (P=0.007), whereas control animals have an increased T4×SV. Upon combination with radiotherapy, the T4×SV of TH-302-treated tumors decrease from 30.8±5.9 (Evofosfamide (TH-302)+radiotherapy) to 25.7±2.9 days (Evofosfamide (TH-302)+radiotherapy+95% O₂)^[3].

storage

Store at -20°C

References

[1] JIAN-XIN DUAN*. Potent and Highly Selective Hypoxia-Activated Achiral Phosphoramidate Mustards as Anticancer Drugs[J]. Journal of Medicinal Chemistry, 2008, 51 8: 2412-2420. DOI: 10.1021/jm701028q
[2] JESSICA D SUN. Selective tumor hypoxia targeting by hypoxia-activated prodrug TH-302 inhibits tumor growth in preclinical models of cancer.[J]. Clinical Cancer Research, 2012, 18 3: 758-770. DOI: 10.1158/1078-0432.ccr-11-1980

N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester manufacturers

Career Henan Chemical Co

Product: N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester 918633-87-1
Price: US $7.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 100kg
Release date: 2020-01-02

918633-87-1, N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl esterRelated Search:

N-Ethyl-3-methylaniline N-ethyl-pyrrolidone N-(2-Hydroxyethyl)-2-pyrrolidone TH287 TH588

N,N'-Bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester

TH 302

EvofosfaMide

TH-302, >=98%

TH-302 (Evofosfamide)

(1-methyl-2-nitro-1H-imidazol-5-yl)methylN,N'-bis(2-bromoethyl)diamidophosphate

EOS-61724

Evofosfamide(TH 302)

EVOFOSFAMID

2-bromo-N-[(2-bromoethylamino)-[(3-methyl-2-nitroimidazol-4-yl)methoxy]phosphoryl]ethanamine

(1-Methyl-2-nitro-1H-imidazol-5-yl)methyl N,N'-bis(2-bromoethyl)phosphorodiamidate

CS-516

TH 302; TH302

Phosphorodiamidic acid, N,N'-bis(2-bromoethyl)-, (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester

HAP-302

Evofosfamide, 10 mM in DMSO

Phosphorodiamidic acid, N,N′-bis(2-bromoethyl)-, (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester (ACI)

Evofosfamide (TH-302) ，S2757

918633-87-1

C9H16Br2N5O4P

TH-302

APIs

API