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Home> Encyclopedia >   /  Cardiovascular Agents  /  Pharmaceutical Intermediates  /  Pharmaceutical  /  Other Chemicals  /  Other Inorganic Chemicals
Benfotiamine structure
Benfotiamine structure

Benfotiamine

Iupac Name:S-[(Z)-2-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-5-phosphonooxypent-2-en-3-yl] benzenecarbothioate
CAS No.: 22457-89-2
Molecular Weight:466.449
Modify Date.: 2022-02-11 09:43
Introduction: Vitamin B1 analog. Synthetic S-acyl derivative of Thiamine (T344185). View more+
1. Names and Identifiers
1.1 Name
Benfotiamine
1.2 Synonyms

8088CB BENFOTAMINE (S-BENZOYLTHIAMINE-O-MONOPHOSPHATE) Benfothiamine benphothiamine Benzenecarbothioic acid, S-[2-[[(4-amino-2-methyl-5-pyrimidinyl)methyl]formylamino]-1-[2-(phosphonooxy)ethyl]-1-propen-1-yl] ester Benzenecarbothioic acid, S-[2-[[(4-amino-2-methyl-5-pyrimidinyl)methyl]formylamino]-1-[2-(phosphonooxy)ethyl]-1-propenyl] ester Benzoic acid, thio-, S-ester with N-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-N-(4-hydroxy-2-mercapto-1-methyl-1-butenyl)formamide dihydrogen phosphate (ester) Benzoylthiamine monophosphate Benzoylthiamine O-monophosphate benzoylthiamineo-monophosphate berdi betivina Bietamine Biotamin BTMP Formamide, N-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-N-(4-hydroxy-2-mercapto-1-methyl-1-butenyl)-, S-benzoate O-(dihydrogen phosphate) Milgamma N-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-N-(4-hydroxy-2-mercapto-1-methyl-1-butenyl)formamide S-benzoate O-phosphate Neurostop Nitanevril S-[2]-[(4-Amino-2-methyl-5-pyrimidinyl)methy-[formylamino]-1-[2-phosphonoxy)ethyl]-1-propenyloic ester phenylcarbathionoic acid S-Benzoylthiamine monophosphate S-Benzoylthiamine O-Monophosphate Tabiomyl Thiobenzoic acid S-[2-[[(4-amino-2-methyl-5-pyrimidinyl)methyl]formylamino]-1-[2-(phosphonooxy)ethyl]-1-propenyl] Thiobenzoic acid S-[2-[[(4-amino-2-methyl-5-pyrimidinyl)methyl]formylamino]-1-[2-(phosphonooxy)ethyl]-1-propenyl] ester Vitanevril

1.3 CAS No.
22457-89-2
1.4 CID
3032771
1.5 EINECS(EC#)
245-013-4
1.6 Molecular Formula
C19H23N4O6PS (isomer)
1.7 Inchi
InChI=1S/C19H23N4O6PS/c1-13(23(12-24)11-16-10-21-14(2)22-18(16)20)17(8-9-29-30(26,27)28)31-19(25)15-6-4-3-5-7-15/h3-7,10,12H,8-9,11H2,1-2H3,(H2,20,21,22)(H2,26,27,28)/b17-13-
1.8 InChkey
BTNNPSLJPBRMLZ-LGMDPLHJSA-N
1.9 Canonical Smiles
CC1=NC=C(C(=N1)N)CN(C=O)C(=C(CCOP(=O)(O)O)SC(=O)C2=CC=CC=C2)C
1.10 Isomers Smiles
CC1=NC=C(C(=N1)N)CN(C=O)/C(=C(/CCOP(=O)(O)O)\SC(=O)C2=CC=CC=C2)/C
2. Properties
3.1 Density
1.444
3.1 Melting point
165 °C
3.1 Boiling point
745.1 °C at 760 mmHg
3.1 Refractive index
1.645
3.1 Flash Point
404.4 °C
3.1 Vapour pressure
2.55E-23mmHg at 25°C
3.1 Precise Quality
466.10800
3.1 PSA
191.05000
3.1 logP
3.84720
3.1 Appearance
shinning black powder
3.2 Chemical Properties
crystals
3.3 pKa
1.84±0.10(Predicted)
3.4 Water Solubility
soluble in water
3.5 StorageTemp
2-8°C
3. Use and Manufacturing
4.1 Definition
ChEBI: A thioester that is a synthetic analogue of thiamine obtained by acylative cleavage of the thiazole ring and O-phospohorylation.
4.2 Usage
Vitamin B1 analog. Synthetic S-acyl derivative of Thiamine (T344185).
4. Safety and Handling
5.1 Hazard Codes
Xn
5.1 Risk Statements
R20/21/22
5.1 Safety Statements
26-36
5.1 WGK Germany
2
5.1 RTECS
DH6910000
5.1 Specification

The IUPAC name of?Benfotiamine?S-[(Z)-2-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-5-phosphonooxypent-2-en-3-yl] benzenecarbothioate. With the?CAS registry number 22457-89-2,?it is also named as S-Benzoylthiamine O-monophosphate.?The classification codes are?Adjuvants, immunologic;?Chelating agents;?Drug / Therapeutic Agent;?Immunologic Factors.?Additionally,?it is?white crystalline powder which is soluble in water.?Benfotiamine is a synthetic S-acyl derivative of thiamine (vitamin B1).

The other characteristics of this product can be summarized as:?(1)ACD/LogP: 1.81; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -0.91; (4)ACD/LogD (pH 7.4): -2.37; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 10; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 10; (12)Index of Refraction: 1.645; (13)Molar Refractivity: 117.14 cm3; (14)Molar Volume: 322.9 cm3; (15)Polarizability: 46.44×10-24 cm3; (16)Surface Tension: 73.3 dyne/cm; (17)Enthalpy of Vaporization: 114.01 kJ/mol; (18)Vapour Pressure: 2.55E-23 mmHg at 25°C; (19)Rotatable Bond Coun: 10; (20)Tautomer Count: 3; (21)Exact Mass: 466.107592; (22)MonoIsotopic Mass: 466.107592; (23)Topological Polar Surface Area: 181; (24)Heavy Atom Count: 31.

Uses of Benfotiamine:?It?is mainly used as an "anti-AGE" supplement.?When combined?with pyridoxine hydrochloride,?it is?used?to treat patients with nerve damage and nerve pain such as sciatica.?In addition,?benfotiamine?is also?effective for the treatment of diabetic retinopathy, neuropathy, and nephropathy.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed,?but also?irritating to eyes, respiratory system and skin.?In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure.
1. SMILES:O=P(O)(O)OCCC(SC(=O)c1ccccc1)=C(N(C=O)Cc2cnc(nc2N)C)C
2.?InChI:InChI=1/C19H23N4O6PS/c1-13(23(12-24)11-16-10-21-14(2)22-18(16)20)17(8-9-29-30(26,27)28)31-19(25)15-6-4-3-5-7-15/h3-7,10,12H,8-9,11H2,1-2H3,(H2,20,21,22)(H2,26,27,28)

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 2200mg/kg (2200mg/kg) ? "Modern Pharmaceuticals of Japan, III," Tokyo, Japan Pharmaceutical, Medical and Dental Suppl Exporters' Assoc., 1968Vol. -, Pg. 78, 1968.
mouse LD50 oral 15gm/kg (15000mg/kg) ? Drugs in Japan Vol. 6, Pg. 781, 1982.

5.2 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DH6910000
CHEMICAL NAME :
Benzoic acid, thio-, S-ester with N-((4-amino-2-methyl-5-pyrimidinyl)methyl)-N-(4-hydro xy- 2-mercapto-1-methyl-1-butenyl)formamide dihydrogen phosphate (ester)
CAS REGISTRY NUMBER :
22457-89-2
LAST UPDATED :
199612
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C19-H23-N4-O6-P-S
MOLECULAR WEIGHT :
466.49
WISWESSER LINE NOTATION :
T6N CNJ B1 DZ E1VMY1&UYSVR&2OPQQO

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
15 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: 6,781,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85IPAE "Modern Pharmaceuticals of Japan, III," Tokyo, Japan Pharmaceutical, Medical and Dental Supply Exporters' Assoc., 1968 Volume(issue)/page/year: -,78,1968
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s) no data available
Signal word

no data available

Hazard statement(s)

no data available

Precautionary statement(s)
Prevention

no data available

Response

no data available

Storage

no data available

Disposal

no data available

2.3 Other hazards which do not result in classification

no data available

6. Computational chemical data
  • Molecular Weight: 466.449g/mol
  • Molecular Formula: C19H23N4O6PS
  • Compound Is Canonicalized: True
  • XLogP3-AA: 0.5
  • Exact Mass: 466.10759264
  • Monoisotopic Mass: 466.10759264
  • Complexity: 697
  • Rotatable Bond Count: 10
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 10
  • Topological Polar Surface Area: 181
  • Heavy Atom Count: 31
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
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