Acetaminophen
- CAS No.
- 103-90-2
- Chemical Name:
- Acetaminophen
- Synonyms
- PARACETAMOL;APAP;4-ACETAMIDOPHENOL;N-(4-HYDROXYPHENYL)ACETAMIDE;PARACETAMOL POWDER;Panadol;Acetaminofen;PARACETAMOL DC96;TYLENOL;excedrin
- CBNumber:
- CB1413658
- Molecular Formula:
- C8H9NO2
- Molecular Weight:
- 151.16
- MOL File:
- 103-90-2.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/7/4 21:45:01
| Melting point | 168-172 °C(lit.) |
|---|---|
| Boiling point | 273.17°C (rough estimate) |
| Density | 1,293 g/cm3 |
| vapor pressure | 0.008Pa at 25℃ |
| refractive index | 1.5810 (rough estimate) |
| Flash point | 11 °C |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | ethanol: soluble0.5M, clear, colorless |
| pka | 9.86±0.13(Predicted) |
| form | Crystals or Crystalline Powder |
| color | White |
| PH | 5.5-6.5 (H2O, 20℃)(saturated solution) |
| PH Range | 5.5 - 6.5 (H?O, 20 °C) (saturated solution) |
| Odor | odorless |
| explosive limit | 15%(V) |
| Water Solubility | 14 g/L (20 ºC) |
| Merck | 14,47 |
| BRN | 2208089 |
| BCS Class | 3,4 |
| InChIKey | RZVAJINKPMORJF-UHFFFAOYSA-N |
| LogP | 1.098 at 25℃ |
| CAS DataBase Reference | 103-90-2(CAS DataBase Reference) |
| IARC | 3 (Vol. 50, 73) 1999 |
| NIST Chemistry Reference | Acetaminophen(103-90-2) |
| EPA Substance Registry System | Acetaminophen (103-90-2) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H302 | |||||||||
| Precautionary statements | P264-P270-P301+P312-P501 | |||||||||
| Hazard Codes | Xn,T,F | |||||||||
| Risk Statements | 22-36/37/38-52/53-36/38-40-39/23/24/25-23/24/25-11 | |||||||||
| Safety Statements | 26-36-61-37/39-22-45-36/37-16-7 | |||||||||
| RIDADR | UN 3077 9/PG III | |||||||||
| WGK Germany | 1 | |||||||||
| RTECS | AE4200000 | |||||||||
| Autoignition Temperature | 540 °C | |||||||||
| TSCA | Yes | |||||||||
| HazardClass | 9 | |||||||||
| PackingGroup | III | |||||||||
| HS Code | 29242930 | |||||||||
| Toxicity | LD50 in mice (mg/kg): 338 orally (Starmer), 500 i.p. (Dahlin, Nelson) | |||||||||
| NFPA 704 |
|
Acetaminophen price More Price(18)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | PHR1005 | Acetaminophen Pharmaceutical Secondary Standard; Certified Reference Material | 103-90-2 | 1G | ₹8530.1 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | PHR1005 | Acetaminophen Pharmaceutical Secondary Standard; Certified Reference Material | 103-90-2 | 10G | ₹52988.38 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | A7085 | Acetaminophen BioXtra, ≥99.0% | 103-90-2 | 100G | ₹6462.53 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | A7085 | Acetaminophen BioXtra, ≥99.0% | 103-90-2 | 500G | ₹15479.75 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | A7085 | Acetaminophen BioXtra, ≥99.0% | 103-90-2 | 1KG | ₹17114.33 | 2022-06-14 | Buy |
Acetaminophen Chemical Properties,Uses,Production
Description
Acetaminophen differs from the nonsteroidal anti-inflammatory agents described in that it is devoid of anti-inflammatory and antirheumatic properties. It was recently shown that acetaminophen, like aspirin, inhibits cyclooxygenase action in the brain and is even stronger than aspirin. On the other hand, the mechanism of analgesic action of acetaminophen is not fully clear, since it acts poorly on peripheral cyclooxygenase.
Chemical Properties
White Solid
Uses
Acetaminophen is widely used as an analgesic and fever-reducing agent. Acetaminophen is designed for moderate analgesia. It is also effective like aspirin and is used in analgesia for headaches (from weak to moderate pain), myalgia, arthralgia, chronic pain, for oncological and post-operational pain, etc.
Indications
Acetaminophen (Tylenol) is an effective antipyretic and analgesic that is well tolerated at therapeutic doses. It has only weak antiinflammatory activity; thus, it is not useful in the treatment of rheumatoid arthritis and other inflammatory conditions.
World Health Organization (WHO)
Paracetamol, a widely used analgesic and antipyretic is known, in case of overdose, to cause liver damage, frequently with fatal outcome. In recommended dosages this risk does not occur. Paracetamol is listed in the WHO Model List of Essential Drugs.
General Description
Odorless white crystalline solid. Bitter taste. pH (saturated aqueous solution) about 6.
Air & Water Reactions
Slightly soluble in water.
Reactivity Profile
Acetaminophen is sensitive to light. Incompatible with strong oxidizers.
Fire Hazard
Flash point data for Acetaminophen are not available; however, Acetaminophen is probably combustible.
Biological Activity
Cyclooxygenase inhibitor; may be selective for COX-3 (IC 50 values are 460, > 1000 and > 1000 μ M for canine COX-3, and murine COX-1 and COX-2 respectively). Widely used analgesic and antipyretic agent.
Mechanism of action
The mechanism of action of paracetamol is not well understood, but it may act in a similar fashion to NSAIDs, with inhibition of cyclo-oxygenase enzymes COX-1 and COX-2 to reduce the phenoxyl radical formation required for COX-1 and 2 activity and prostaglandin synthesis. I t has selectivity for inhibition of prostaglandin synthesis with low concentrations of peroxidases and arachidonic acid, but limited effect at higher concentrations and, therefore, has limited anti-inflammatory effects. Unlike opioids, paracetamol has no well-defined endogenous binding sites. I n some circumstances, it may exhibit a preferential effect on COX-2 inhibition. There is growing evidence of a central antinociceptive effect of paracetamol. It has also been found to prevent prostaglandin production at the cellular transcriptional concentration, independent of COX activity.
Pharmacokinetics
Paracetamol is absorbed rapidly from the small intestine after oral
administration; peak plasma concentrations are reached after 30–60min. It
may also be given rectally and intravenously (either as paracetamol or the
prodrug propacetamol). It has good oral bioavailability (70%–90%); rectal absorption is more variable (bioavailability ~50%–80%) with a longer time to
reach peak plasma concentration. The plasma half-life is approximately 2–3 h.
Paracetamol is metabolised by hepatic microsomal enzymes mainly to the
glucuronide, sulphate and cysteine conjugates. None of these metabolites is
pharmacologically active. Aminimal amount of the metabolite N-acetyl-pamino-
benzoquinone imine is normally produced by cytochrome P450–
mediated hydroxylation. This reactive toxic metabolite is rendered harmless
by conjugation with liver glutathione, then excreted renally as mercapturic
derivatives. With larger doses of paracetamol, the rate of formation of the
reactive metabolite exceeds that of glutathione conjugation, and the reactive
metabolite combines with hepatocellular macromolecules, resulting in cell
death and potentially fatal hepatic failure. The formation of this metabolite is
increased by drugs inducing cytochrome P450 enzymes, such as barbiturates
or carbamazepine.
Clinical Use
Acetaminophen is weakly acidic (pKa = 9.51) and synthesized by the acetylation of p-aminophenol. It is weakly bound to plasma proteins (18–25%). Acetaminophen is indicated for use as an antipyretic/analgetic, particularly in those individuals displaying an allergy or sensitivity to aspirin. It does not possess anti-inflammatory activity, but it will produce analgesia in a wide variety of arthritic and musculoskeletal disorders. It is available in various formulations, including suppositories, tablets, capsules, granules, and solutions. The usual adult dose is 325 to 650 mg every 4 to 6 hours. Doses of greater than 2.6 g/day are not recommended for long-term therapy because of potential hepatotoxicity issues. Acetaminophen, unlike aspirin, is stable in aqueous solution, making liquid formulations readily available, a particular advantage in pediatric cases.
Metabolic pathway
Acetaminophen (APAP) is metabolized by mice, and nine metabolites are identified in the urine. The main metabolites are APAP-glucuronide and 3-cysteinyl- APAP. Hydroquinone metabolites of S-(2,5- dihydroxyphenyl)cysteine and S-(2,5-dihydroxyphenyl)- N-acetylcysteine result from the benzoquinone metabolite of APAP.
Metabolism
acetaminophen is undergoes rapid first-pass metabolism in the GI tract primarily by conjugation reactions, with the O-sulfate conjugate being the primary metabolite in children and the O-glucuronide being the primary metabolite in adults. A minor, but significant, product of both acetaminophen and phenacetin is the N-hydroxyamide produced by a CYP2E1 and CYP3A4.
Purification Methods
Recrystallise Paracetamol from water or EtOH. The 3,5-dinitrobenzamide complex gives orange crystals from hot H2O and has m 171.5o. [Beilstein 13 H 460, 13 I 159, 13 II 243, 13 III 1056, 13 IV 1091.]
Acetaminophen Preparation Products And Raw materials
Raw materials
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chevron_right| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| OPULENT PHARMA | +91-9106692785 +91-9106692785 | Gujarat, India | 479 | 58 | Inquiry |
| ANWITA APIS | +919000311012 | Hyderabad, India | 198 | 58 | Inquiry |
| SNECOFRi Pvt Ltd | +91-9032850129 +91-9032850129 | Telangana, India | 404 | 58 | Inquiry |
| Frolic Pharmachem | +919711094561 | Himachal Pradesh, India | 94 | 58 | Inquiry |
| AARTIA KEM SCIENCE | +91-8291072530 +91-8291072530 | Maharashtra, India | 70 | 58 | Inquiry |
| KARPSCHEM LABORATORIES | +91-7249203006 +91-7249203006 | Maharashtra, India | 786 | 58 | Inquiry |
| Globus Pharmachem (Para Products Pvt Ltd) | +91-1204198900 +91-9899370547 | Uttar Pradesh, India | 22 | 58 | Inquiry |
| Panoli Intermediates (India) Pvt., Limited. (Kutch Chemical Industries Ltd.) | +91-2652397013 +91-7226032610 | Gujarat, India | 45 | 58 | Inquiry |
| Smilax Laboratories Limited | +91-8919514965 +91-8008333438 | Telangana, India | 28 | 58 | Inquiry |
| Meghmani Unichem LLP | +91-9879606352 +91-9879606353 | Gujarat, India | 1 | 58 | Inquiry |
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