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Home> Encyclopedia >   /  Pharmaceutical Intermediates  /  Pharmaceutical  /  Organic Intermediate
Posaconazole structure
Posaconazole structure

Posaconazole

Iupac Name:4-[4-[4-[4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1,2,
4-triazol-1-ylmethyl)oxolan-3-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-
2-[(2S,3S)-2-hydroxypentan-3-yl]-1,2,4-triazol-3-one
CAS No.: 171228-49-2
Molecular Weight:700.777386
Modify Date.: 2022-11-12 07:05
Introduction: Posaconazole, launched in the UK, is the newest member of the azoleclass of antifungal agents to reach the market. It is indicated for the treatment andprophylaxis of a range of invasive fungal infections, including aspergillosis,fusariosis, chromoblastomycosis, mycetoma, and coccidiomycosis in patientswho are refractory to, or intolerant of, standard therapy with amphotericin Band/or itraconazole. In the US, it is approved for the prophylaxis of invasiveAspergillus and Candida infections in patients 13 years of age who are at highrisk of developing these infections due to being severely immunocompromised.Additionally, it is approved for the treatment of oropharyngeal candidiasis.Posaconazole has an expanded spectrum of activity over other members of theazole antifungals. In addition to potent activity against refractory cases ofaspergillosis and fluconazole-resistant Candida, it demonstrates activity againstZygomycetes. View more+
1. Names and Identifiers
1.1 Name
Posaconazole
1.2 Synonyms

2,5-Anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-[[4-[4-[4-[1-[(1S,2S)-1-ethyl-2-hydroxypropyl]-1,5-dihydro-5-oxo-4H-1,2,4-triazol-4-yl]phenyl]-1-piperazinyl]phenoxy]methyl]-1-(1H-1,2,4-triazol-1-yl)-D-threo-pentitol 4-(4-(4-(4-(((3R,5R)-5-((1H-1,2,4-Triazol-1-yl)methyl)-5-(2,4-difluorobenzyl)tetrahydrofuran-3 4-(4-(4-(4-(((3R,5R)-5-((1H-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-2-((2S,3S)-2-hydroxypentan-3-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one D-threo-Pentitol, 2,5-anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-[[4-[4-[4-[1-[(1S,2S)-1-ethyl-2-hydroxypropyl]-1,5-dihydro-5-oxo-4H-1,2,4-triazol-4-yl]phenyl]-1-piperazinyl]phenoxy]methyl]-1-(1H-1,2,4-triazol-1-yl)- HYDROXYPROPYL]-2,4-DIHYDRO-3H-1,2,4-TRIAZOL-3-ONE Noxafil Posaconazole SP Sch 56592

1.3 CAS No.
171228-49-2
1.4 CID
468595
1.5 EINECS(EC#)
200-659-6
1.6 Molecular Formula
C37H42F2N8O4 (isomer)
1.7 Inchi
InChI=1S/C37H42F2N8O4/c1-3-35(26(2)48)47-36(49)46(25-42-47)31-7-5-29(6-8-31)43-14-16-44(17-15-43)30-9-11-32(12-10-30)50-20-27-19-37(51-21-27,22-45-24-40-23-41-45)33-13-4-28(38)18-34(33)39/h4-13,18,23-27,35,48H,3,14-17,19-22H2,1-2H3/t26-,27+,35-,37-/m0/s1
1.8 InChkey
RAGOYPUPXAKGKH-XAKZXMRKSA-N
1.9 Canonical Smiles
CCC(C(C)O)N1C(=O)N(C=N1)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)OCC5CC(OC5)(CN6C=NC=N6)C7=C(C=C(C=C7)F)F
1.10 Isomers Smiles
CC[C@@H]([C@H](C)O)N1C(=O)N(C=N1)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)OC[C@H]5C[C@](OC5)(CN6C=NC=N6)C7=C(C=C(C=C7)F)F
2. Properties
2.1 Density
1.36
2.1 Melting point
170-1720C
2.1 Boiling point
850.7 °C at 760 mmHg
2.1 Refractive index
1.657
2.1 Flash Point
468.3 °C
2.1 Precise Quality
700.33000
2.1 PSA
115.70000
2.1 logP
4.70320
2.1 Solubility
In water, 0.027 mg/L at 25 deg C (est)
2.2 Appearance
White solid
2.3 Storage
-20°C Freezer
2.4 Chemical Properties
White Solid
2.5 Color/Form
White solid
2.6 pKa
14.72±0.20(Predicted)
2.7 Water Solubility
In water, 0.027 mg/L at 25 deg C (est)
2.8 StorageTemp
<0°C
3. Use and Manufacturing
3.1 Definition
ChEBI: An N-arylpiperazine that consists of piperazine carrying two 4-substituted phenyl groups at positions 1 and 4. A triazole antifungal drug.
3.2 Usage
Orally active triazole antifungal.
4. Safety and Handling
4.1 Hazard Codes
F,T
4.1 Risk Statements
11-23/24/25-39/23/24/25
4.1 Safety Statements
7-16-36/37-45
4.1 Octanol/Water Partition Coefficient
log Kow = 4.77 at 25 deg C (est)
4.2 DisposalMethods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
4.3 RIDADR
UN1230 - class 3 - PG 2 - Methanol, solution
4.3 WGK Germany
3
4.3 RTECS
XZ5481020
4.3 Toxicity
Organic Compound; Amine; Organofluoride; Ether; Drug; Antifungal Agent; Antibiotic, Antifungal; Metabolite; Trypanocidal Agent; Synthetic Compound
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Carcinogenicity, Category 2

Reproductive toxicity, Category 2

Specific target organ toxicity \u2013 repeated exposure, Category 1

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H351 Suspected of causing cancer

H361 Suspected of damaging fertility or the unborn child

H372 Causes damage to organs through prolonged or repeated exposure

H400 Very toxic to aquatic life

H410 Very toxic to aquatic life with long lasting effects

Precautionary statement(s)
Prevention

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P260 Do not breathe dust/fume/gas/mist/vapours/spray.

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P273 Avoid release to the environment.

Response

P308+P313 IF exposed or concerned: Get medical advice/ attention.

P314 Get medical advice/attention if you feel unwell.

P391 Collect spillage.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

6. NMR Spectrum
9. Other Information
9.0 Merck
14,7602
9.1 Pharmacological effects
Posaconazole (posaconazole) is derived from itraconazole. It is currently subject to III phase clinical trials. Its pharmacological effects are similar with azoles, but compared with itraconazole, it has a stronger inhibitory effect on the C14 demethylation of steroid, especially for Aspergillus.
9.2 Clinical indications and usage
It can be clinically used for the treatment of aspergillosis, zygnmycosis, and fusariumsis and can also be used for infection caused by part of fluconazole-resistant Candida genus. Studies have shown that posaconazole can widely and effectively applied to the treatment of phaeohyphomycosis and improve the infection survival rate of dermatitidis infection in a dose-dependent manner. The drug, as second-line drugs, has an effective rate of 44% to 78% against the invasive aspergillosis which is resistant to amphotericin B and itraconazole. It also has an effective rate of 71% against the zygomycete fungi. The drug is an oral suspension with the recommended dose of 200mg and 4 times per day with meals and taken orally for 7 to 10 days. This dose can also be maintained or changed to 400mg with oral administration of 2 times per day. The steady-state plasma concentration can reach within 7 to 10 days.
9.3 Chemical Properties
White Solid
9.4 Uses
Orally active triazole antifungal.
9.5 Uses
Posaconazole is a sterol C14ɑ demethylase inhibitor with an IC50 of 0.25 nM
9.6 Definition
ChEBI: An N-arylpiperazine that consists of piperazine carrying two 4-substituted phenyl groups at positions 1 and 4. A triazole antifungal drug.
9.7 Antimicrobial activity
The spectrum includes dimorphic fungi (Blast. dermatitidis, Coccidioides spp., Hist. capsulatum, Pen. marneffei, and Spor. schenckii), molds (Aspergillus spp., Mucor spp., Rhizomucor spp. and Rhizopus spp.), some dematiaceous fungi and yeasts (Candida spp. and Cryptococcus spp.).
9.8 Pharmaceutical Applications
A synthetic triazole available for oral administration.
9.9 Pharmacokinetics
Cmax 200 mg oral: 0.5 mg/L after 4 h
Plasma half-life: 35 h
Volume of distribution: 1774 L
Plasma protein binding: >98%
Absorption
Oral absorption is slow. Absorption from the gastrointestinal tract is improved if the drug is given with a high-fat meal. Blood concentrations increase in proportion to dosage up to 800 mg.
Distribution
It is extensively distributed into body tissues.
Metabolism and excretion
It is not as extensively metabolized by the hepatic cytochrome P450 system as other triazole antifungals. More than 70% of an administered dose is eliminated in the feces, predominantly as unchanged drug. The remainder is excreted as glucuronidated derivatives in the urine. Posaconazole is a substrate for intestinal P-glycoprotein,an adenosine triphosphate-dependent plasma membrane transporter responsible for drug efflux from cells. Multiple peaks in blood concentrations have been observed, suggesting that effluxed drug is reabsorbed into the systemic circulation.
9.10 Clinical Use
Invasive aspergillosis
Fusarium infection
Chromoblastomycosis and mycetoma
Coccidioidomycosis
Oropharyngeal candidosis
Prophylaxis of invasive fungal infections in patients at serious risk
With the exception of oropharyngeal candidosis and prophylaxis, use is presently restricted to patients with disease that is refractory to other antifungal drugs, or who are intolerant to them.
9.11 Side effects
It is generally well tolerated even for long periods. Unwanted effects include gastrointestinal discomfort and mild to moderate, transient abnormalities of liver enzymes. Rare side effects include cholestasis and hepatic failure.
10. Computational chemical data
  • Molecular Weight: 700.777386g/mol
  • Molecular Formula: C37H42F2N8O4
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 700.32970817
  • Monoisotopic Mass: 700.32970817
  • Complexity: 1170
  • Rotatable Bond Count: 12
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 11
  • Topological Polar Surface Area: 112
  • Heavy Atom Count: 51
  • Defined Atom Stereocenter Count: 4
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADcfB/+YAAAAAAAAAAAAAAAAAAAWJEAAA8YMEAAAAAAAAB1AAAHwAICAAADXzhmA431ocIFgCqAiRDdACSCAsxooAfyAAObIiOfiLEuZuXeCjtxhPY6Cfw0PIOgECAAAAAAAAAgQAAAAAAAAAAAAAAAA==
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