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(+)-Ibuprofen

(+)-Ibuprofen structure

CAS No:
51146-56-6
Formula:
C13H18O2
Chemical Name:
(+)-Ibuprofen
Synonyms:
Benzeneacetic acid,α-methyl-4-(2-methylpropyl)-,(αS)-;Benzeneacetic acid,α-methyl-4-(2-methylpropyl)-,(S)-;(αS)-α-Methyl-4-(2-methylpropyl)benzeneacetic acid;(+)-Ibuprofen;d-Ibuprofen;(S)-(+)-Ibuprofen;(S)-Ibuprofen;Dexibuprofen;(+)-(S)-Ibuprofen;(+)-Ibuprophen;(S)-2-(4-Isobutylphenyl)propionic acid;(S)-2-(4-Isobutylphenyl)propanoic acid;(+)-(S)-p-Isobutylhydratropic acid;(S)-2-(p-Isobutylphenyl)propionic acid;(+)-α-Methyl-4-(2-methylpropyl)benzeneacetic acid;(S)-(+)-4-Isobutyl-α-methylphenylacetic acid;(S)-(+)-2-(4-Isobutylphenyl)propionic acid;Seractil;(S)-(+)-p-Isobutylhydratropic acid;Nyfen;Ultraprofen;S-Optifen
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

(S)-(+)-Ibuprofen is the S-enantiomer of Ibuprofen. Ibuprofen is an anti-inflammatory inhibitor targeting COX-1 and COX-2 with IC50 of 13 μM and 370 μM, respectively.

Dexibuprofen is an ibuprofen. It has a role as a non-narcotic analgesic and a non-steroidal anti-inflammatory drug. It is an enantiomer of a levibuprofen.|Dexibuprofen, S(+)-ibuprofen, is a non-steroidal anti-inflammatory drug (NSAID). It is a pharmacologically effective enantiomer of racemic ibuprofen that differs in physicochemical properties. It is proposed to be more pharmacologically active and tolerable with a better safety profile than ibuprofen due to higher concentration of active S enantiomer. Dexibuprofen has a slower dissolution rate in the simulated gastric and enteric juices compared with the racemic ibuprofen and displays improved oral bioavilability. For Metabolism, Enzymes, Carriers, Transporters Sections, refer to [Ibuprofen].

(+)-Ibuprofen Basic Attributes

Molecular Weight：

206.28

Exact Mass：

206.28

UNII：

671DKG7P5S

NSC Number：

759814

DSSTox ID：

DTXSID9048724

ATC Code：

M - Musculo-skeletal system

HScode：

2916399090

Characteristics

PSA：

37.3

XLogP3：

3.5

Appearance：

colourless, crystalline solid

Density：

1.0±0.1 g/cm3

Melting Point：

54 °C

Boiling Point：

110 °C @ Press: 0.1 Torr

Flash Point：

216.7±14.4 °C

Refractive Index：

1.519

Water Solubility：

insoluble

Storage Conditions：

Store at RT

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R22;R63

safety instructions：

S36/37-S45

Marks：

Xn:Harmful;

Stability/Shelf Life：

Stable. Incompatible with strong oxidizing agents.

Precautionary statement(s)：

P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (85.71%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 7 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity Summary：

Oral LD50 value in rats is 636 mg/kg. For more information, refer to [ibuprofen].

Protein Binding：

For more information, refer to [ibuprofen].

Drug Information

Drug Indication：

For more information, refer to [ibuprofen].

Pharmacology：

For more information, refer to [ibuprofen].

Absorption：

The time it take to reach peak plasma concentration is 2.25-5 hours post-administration of oral tablets containing 300mg of dexibuprofen. For more information, refer to [ibuprofen].|Mainly renal excretion. For more information, refer to [ibuprofen].|For more information, refer to [ibuprofen].

Metabolism/Metabolites：

For more information, refer to [ibuprofen].|(S)-(+)-ibuprofen has known human metabolites that include 2-Hydroxyibuprofen and 3-Hydroxyibuprofen.

Biological Half-Life：

Oral tablets containing 300mg of dexibuprofen results in 2.2-4.7 hours. For more information, refer to [ibuprofen].

Mechanism of Action：

Like common NSAIDs, dexibuprofen is an active enantiomer of [ibuprofen] that suppresses the prostanoid synthesis in the inflammatory cells via inhibition of the COX-2 isoform of the arachidonic acid COX. For more information, refer to [ibuprofen].

MeSH Entry Terms：

dexibuprofen

(+)-Ibuprofen Use and Manufacturing

Uses

A nonsteroidal anti-inflammatory drug (NSAID); activity resides primarily in the (S)-isomer sedative Ibuprofen is a non-steroidal anti-inflammatory drug with diverse biochemical actions, most notably inhibiting COX-1 and COX-2 (IC50s = 2.6 and 1.53, μM, respectively). It is commonly synthesized as a racemic mixture of (S)- and (R)-isomers. (S)-Ibuprofen is an enantiomer that more potently inhibits COX activity, thromboxane formation, and platelet aggregation than the (R)-form. (S)-Ibuprofen also inhibits activation of NF-κB more effectively than (R)-ibuprofen (IC50s = 62 and 122 μM, respectively). However, the enantiomers are equipotent in blocking superoxide formation, β-glucuronidase release, and LTB4 generation by stimulated neutrophils (IC50 values range from 0.14 to 0.58 μM). A majority of (R)-ibuprofen can be inverted to (S)-ibuprofen in humans after oral administration.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:206.28
XLogP3:3.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:206.130679813
Monoisotopic Mass:206.130679813
Topological Polar Surface Area:37.3
Heavy Atom Count:15
Complexity:203
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

By inhibiting the synthesis of prostaglandins or other inflammatory mediators, it exhibits anti-inflammatory, analgesic and antipyretic effects. It is more potent than ibuprofen and takes effect more quickly.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Dexibuprofen Capsules
Ingredients	The main ingredient of this product is dexibuprofen.
Indication	1. When used with other non-steroidal anti-inflammatory drugs, it increases gastrointestinal side effects and has the risk of causing ulcers. Long-term use with acetaminophen may increase toxic side effects on the kidneys. 2. When used with aspirin or other salicylic acid drugs, the efficacy is not enhanced, but the incidence of gastrointestinal adverse reactions and bleeding tendency increases. 3. When used with anticoagulants such as heparin and dicoumarol and platelet aggregation inhibitors, there is an increased risk of bleeding. 4. When used with furosemide, the latter's sodium excretion and antihypertensive effects are weakened. 5. When used with verapamil and nifedipine, the blood concentration of this product increases. 6. This product can increase the blood concentration of digoxin. When used together, it is necessary to pay attention to adjusting the dose of digoxin. 7. This product can enhance the effect of antidiabetic drugs (including oral hypoglycemic drugs). 8. This product can affect when used with antihypertensive drugs
Specifications	0.15g
Manufacturer	Suzhou NO.4 Pharmaceutical FACTORY Co., Ltd.

Registered Holders

SMS Pharmaceuticals Ltd

United States
Active
SMS PHARMACEUTICALS LIMITED

India
Active
SOLARA ACTIVE PHARMA SCIENCES LIMITED

Brazil
Active

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