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Tox21_300140

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Also known as: 108-46-3, Benzene-1,3-diol, 1,3-benzenediol, Resorcin, 1,3-dihydroxybenzene, M-hydroquinone

Molecular Formula

C₆H₆O₂

Molecular Weight

110.11 g/mol

InChI Key

GHMLBKRAJCXXBS-UHFFFAOYSA-N

FDA UNII

YUL4LO94HK

resorcinol is a natural product found in Anacardium occidentale, Dothiorella vidmadera, and other organisms with data available.

1 2D Structure

Resorcinol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

benzene-1,3-diol

2.1.2 InChI

InChI=1S/C6H6O2/c7-5-2-1-3-6(8)4-5/h1-4,7-8H

2.1.3 InChI Key

GHMLBKRAJCXXBS-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC(=CC(=C1)O)O

2.2 Other Identifiers

2.2.1 UNII

YUL4LO94HK

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Resorcin

2. Resorcinol Disodium Salt

3. Resorcinol, Monocopper (2+) Salt

2.3.2 Depositor-Supplied Synonyms

1. 108-46-3

2. Benzene-1,3-diol

3. 1,3-benzenediol

4. Resorcin

5. 1,3-dihydroxybenzene

6. M-hydroquinone

7. M-hydroxyphenol

8. M-dihydroxybenzene

9. 3-hydroxyphenol

10. M-benzenediol

11. Resorcine

12. M-dioxybenzene

13. Dihydroxybenzol

14. Resorzin

15. Developer O

16. Developer R

17. Developer Rs

18. Fouramine Rs

19. Fourrine Ew

20. Pelagol Rs

21. Pelagol Grey Rs

22. Resorcinolum

23. Fourrine 79

24. Nako Tgg

25. C.i. Oxidation Base 31

26. Durafur Developer G

27. Phenol, M-hydroxy-

28. C.i. Developer 4

29. Benzene, M-dihydroxy-

30. Fema No. 3589

31. Rcra Waste Number U201

32. Acnomel

33. Benzene, 1,3-dihydroxy-

34. Rezamid

35. Sulforcin

36. 3-hydroxycyclohexadien-1-one

37. Resorcinum

38. Nci-c05970

39. Rcra Waste No. U201

40. Nsc 1571

41. C.i. 76505

42. .alpha.-resorcinol

43. Resorcin (jan)

44. Resorcin (tn)

45. Resorcinol (usp)

46. Resorcinol [usp]

47. 1,3-benzenediol, Homopolymer

48. Nsc-1571

49. Yul4lo94hk

50. Chembl24147

51. Chebi:27810

52. Resorcinol [un2876] [poison]

53. Mfcd00002269

54. Ncgc00091501-01

55. Resorcin [jan]

56. Benzene,1,3-dihydroxy Resorcinol

57. C.i.-76505

58. Dsstox_cid_1238

59. Dsstox_rid_76030

60. Dsstox_gsid_21238

61. Rco

62. Caswell No. 723

63. Rezorsine

64. Resorcinol (1,3-dihydroxybenzene)

65. Rodol Rs

66. Cas-108-46-3

67. Ccris 4052

68. Hsdb 722

69. Resorcinol, Homopolymer

70. Einecs 203-585-2

71. Unii-yul4lo94hk

72. Un2876

73. Epa Pesticide Chemical Code 071401

74. Brn 0906905

75. Remazol

76. Ai3-03996

77. M-hydroxy-phenol

78. 3-hydroxy-phenol

79. Resorcinol, Acs

80. 3aqt

81. 3-hydroxy Phenol

82. Resorcinol, 8ci

83. Benzen-1,3-diol

84. Resorcinol, Reagent

85. 1,3-benzene Diol

86. Resorcine, Technical

87. 1,3-dihyroxybenzene

88. 1,3-dihydroxybenzol

89. Acnomel (salt/mix)

90. Eskamel (salt/mix)

91. Rezamid (salt/mix)

92. Phenol Derivative, 3

93. 26982-54-7

94. Benzene,3-dihydroxy-

95. Sulforcin (salt/mix)

96. 1,3-dihydroxy-benzene

97. Spectrum_000173

98. M-dihydroxybenzene,(s)

99. Resorcinol [mi]

100. Spectrum2_001310

101. Spectrum3_000895

102. Spectrum4_000990

103. Spectrum5_001152

104. Resorcinol [fhfi]

105. Resorcinol [hsdb]

106. Resorcinol [iarc]

107. Resorcinol [inci]

108. Resorcinum [hpus]

109. Wln: Qr Cq

110. Resorcinol [vandf]

111. Bmse000415

112. Ec 203-585-2

113. Resorcinol [mart.]

114. 1,3-dihydroxybenzene, Xii

115. Nciopen2_003867

116. Resorcinol [usp-rs]

117. Resorcinol [who-dd]

118. Schembl15515

119. Kbiogr_001399

120. Kbioss_000653

121. Resorcinol, >=98%, Fg

122. Resorcinol, Flake, Technical

123. Resorcinol, Lr, >=99%

124. 4-06-00-05658 (beilstein Handbook Reference)

125. Bidd:er0285

126. Divk1c_000041

127. Spectrum1500527

128. Spbio_001379

129. Resorcinol, Bioxtra, >=99%

130. Zinc2028

131. Dtxsid2021238

132. Bdbm26189

133. Fema 3589

134. Hms500c03

135. Kbio1_000041

136. Kbio2_000653

137. Kbio2_003221

138. Kbio2_005789

139. Kbio3_001810

140. Resorcinol, Reagent Grade, 98%

141. Nsc1571

142. Resorcinol [ep Monograph]

143. 4e49

144. Ninds_000041

145. Hms1920p06

146. Hms2092g07

147. Pharmakon1600-01500527

148. Resorcinol [usp Monograph]

149. 1,3-dihydroxybenzene (resorcinol)

150. Hy-b0907

151. Resorcinol, Reagentplus(r), 99%

152. Tox21_111140

153. Tox21_202417

154. Tox21_300140

155. Ccg-39248

156. Nsc757310

157. Resorcinol 10 Microg/ml In Methanol

158. Resorcinol, Crystalline Powder, Usp

159. Stl185604

160. Resorcinol 1000 Microg/ml In Water

161. Akos000119813

162. Resorcinol 100 Microg/ml In Methanol

163. Resorcinol, Acs Reagent, >=99.0%

164. Tox21_111140_1

165. Db11085

166. Nsc-757310

167. Un 2876

168. Idi1_000041

169. Ncgc00091501-02

170. Ncgc00091501-03

171. Ncgc00091501-04

172. Ncgc00091501-05

173. Ncgc00091501-06

174. Ncgc00253918-01

175. Ncgc00259966-01

176. Resorcinol, P.a., 99.0-100.5%

177. Resorcinol, Tested According To Ph.eur.

178. Ac-14363

179. Bp-21158

180. Ls-13122

181. Resorcinol, Saj First Grade, >=98.0%

182. Sbi-0051505.p003

183. Resorcinol, Jis Special Grade, >=99.0%

184. Fluorescein Impurity A [ep Impurity]

185. Ft-0606668

186. Ft-0674352

187. Ft-0674353

188. R0008

189. S4579

190. 1,3-benzenediol; 1,3-dihydroxybenzene

191. C01751

192. D00133

193. Ab00052085_03

194. Hexylresorcinol Impurity B [ep Impurity]

195. A801880

196. Q408865

197. Sr-05000002092

198. Fluorescein Sodium Impurity A [ep Impurity]

199. Q-201666

200. Sr-05000002092-1

201. Brd-k74190368-001-02-7

202. F1908-0097

203. Resorcinol, Certified Reference Material, Tracecert(r)

204. Z955123646

205. Resorcinol, European Pharmacopoeia (ep) Reference Standard

206. Resorcinol, United States Pharmacopeia (usp) Reference Standard

207. Hymecromone Impurity A, European Pharmacopoeia (ep) Reference Standard

208. Resorcinol, Pharmaceutical Secondary Standard; Certified Reference Material

209. Resorcinol, Meets Analytical Specification Of Ph.??eur., Bp, 98.5-100.5% (calc. To The Dried Substance)

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₆H₆O₂
Molecular Weight	110.11 g/mol
XLogP3	0.8
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	110.036779430 g/mol
Monoisotopic Mass	110.036779430 g/mol
Topological Polar Surface Area	40.5 Å²
Heavy Atom Count	8
Formal Charge	0
Complexity	64.9
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

THERAPEUTIC CATEGORY (VETERINARY): Topical antipruritic and antiseptic. Has been used as an intestinal antiseptic

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1514

THERAPEUTIC CATEGORY: Keratolytic; antiseborrheic

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1514

Resorcinol (1,3 benzenediol; m-dihydroxybenzene: resorcin) is a pharmaceutical agent used topically in dermatological treatments such as acne and related skin conditions. It could also be used in combination with the other acne treatment agents such as sulphur...

PMID:15462161 Duran B et al; J Toxicol Clin Toxicol. 42(5):663-6.(2004).

Medication (vet): keratolytic, antipruritic, antiseptic, surfactant. ... Use: ... in various lotions, creams, & ointments. Topically, on eczemas & otitis externa of dogs. Poor antiseptic in presence of particulate matter. Best as aerosol spray germicide.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 510

4.2 Drug Indication

Contemporary therapeutic uses for resorcinol primarily revolve around the use of the phenol derivative as an active ingredient in topical antiseptics or as topical antibacterial skin treatment products for conditions like acne, seborrheic dermatitis, eczema, and others.

5 Pharmacology and Biochemistry

5.1 Pharmacology

In vitro and in vivo studies have demonstrated that resorcinol can inhibit peroxidases in the thyroid and subsequently block the synthesis of thyroid hormones and cause goiter. Resorcinol interferes with the iodination of tyrosine and the oxidation of iodide. In an in vitro study involving lactoperoxidase (LPO) and thyroid peroxidase (TPO), it was shown that the mechanism of these two enzymes can become irreversibly inhibited by way of a suicide inactivation by resorcinol. It is believed that the Fe3+ of the porphyrin residue of the peroxidase to is oxidised to Fe4+ by hydrogen peroxide with the transfer of an oxygen radical. In LPO and TPO, the resulting -cation radical of the porphyrin can isomerize to a radical cation with the radical in an aromatic side chain of the enzyme. The latter radical can bind, in a pH-dependent reaction, covalently and irreversibly to the resorcinol radical formed during regular oxidation of resorcinol and this reduces the activity of the enzyme greatly. While the inactivation of the enzyme and the binding of resorcinol to the enzyme may be largely increased by the presence of 0.1 nM iodide, increasing the iodide concentration to 5 mM reduced the resorcinol binding to the enzyme by one quarter but increased the enzyme activity, determined as the rate of iodination of tyrosine, more than proportionally from 6.2% to 44.7%. Nevertheless, the role played by iodide ions in the irreversible inactivation of the enzymes is not yet fully elucidated. Ultimately, such in vitro and in vivo data propose that the anti-thyroidal activity of resorcinol is caused by inhibition of thyroid peroxidase enzymes, resulting in decreased thyroid hormone production and increased proliferation due to an increase in the secretion of TSH (thyroid stimulating hormone). The iodination process is catalyzed by a haem-containing enzyme, and resorcinol is known to form covalent bonds with haem. Despite the legitimacy of this pharmacodynamic profile in resorcinol, the therapeutic uses for which it may be formally indicated for at this time do not actually rely upon any of these mechanisms or dynamics, which are primarily elicited only upon systemic exposure to resorcinol or particularly high overdosage of the agent. This is especially true, considering resorcinol is most commonly available as topical applications to the public.

5.2 ATC Code

D - Dermatologicals

D10 - Anti-acne preparations

D10A - Anti-acne preparations for topical use

D10AX - Other anti-acne preparations for topical use

D10AX02 - Resorcinol

S - Sensory organs

S01 - Ophthalmologicals

S01A - Antiinfectives

S01AX - Other antiinfectives

S01AX06 - Resorcinol

5.3 Absorption, Distribution and Excretion

Absorption

The dermal absorption of resorcinol seems to be low (< 1%) when applied on healthy and intact skin. The agent absorbed very slightly under normal conditions & the absorption was lower when applied to the scalp than to clean shaven skin due to a strong fixation by the hair.

Route of Elimination

Specific data regarding the route of elimination of resorcinol is not readily available, although the major metabolite of resorcinol found in the urine was its glucuronide.

Volume of Distribution

Specific data regarding the volume of distribution of resorcinol is not readily available, although it is believed that the compound's volume of distribution is considered large, owing to resorcinol's profile as a lipid-soluble compound.

Clearance

Specific data regarding the clearance of resorcinol is not readily available, although it is generally believed that the relatively low topical absorption or resorcinol does not result in an extensive systemic presence and clearance.

A dose of 112 mg/kg of (14)C resorcinol was orally administered to 3 male and 3 female Fischer 344 rats. After one day, the animals were sacrificed, and major tissues and excretory products were analyzed to determine the fate of the resorcinol. Only trace amounts of the compound were found in any tissue and there was no evidence of specific organ accumulation. More than 90% of the total administered dose was recovered from the excreta in 24 hr. The primary route of excretion was in the urine. Only 1 to 2% of the dose was eliminated in the feces and less than 0.1% was eliminated as CO2. Cannulation of the common bile duct followed by iv injection of 11.2 mg/kg resorcinol indicated that excretion in bile was rapid and underwent enterohepatic circulation to be excreted in the urine. Less than 50% of the parent compound was excreted in the urine, most was in the form of four metabolites. The major metabolite of resorcinol was a glucuronide conjugate (approximately 70%). One metabolite was identified as a sulfate conjugate (10-20%), one was identified as a diconjugate with glucuronide and sulfate (5-10%), and one, present in small quantities (less than 2%), was suggested to be a diglucuronide conjugate. Repeated exposure of both sexes to daily doses of 225 mg/kg for 5 days did not alter the rate or relative metabolite ratio of resorcinol excretion.

Kim YC, Matthews HB; Fundam Appl Toxicol 9 (3): 409-14 (l987)

Resorcinol absorbed very slightly under normal conditions & the absorption was lower when applied to the scalp than to clean shaven skin due to a strong fixation by the hair. The results were somewhat similar in humans, rhesus monkeys & guinea pigs.

Maibach HI; Labo-Pharma-Probl Tech 335: 727-9 (1983)

Pharmacokinetic data on resorcinol were obtained from studies in the rat. The drug, administered in an aqueous solution, rapidly cleared plasma via urine and did not accumulate in tissues. In the urine, the major metabolite of resorcinol was its glucuronide. Repeated dosing for 30 days with maximum tolerated daily doses of 100 mg/kg did not alter pharmacokinetic parameters, nor did it cause overt toxic signs or adverse reactions. The animals' body weight, blood values, levels of serum T3 and T4, and the gross and microscopic appearance of the thyroid gland and spinal cord remained within normal limits throughout the study.

PMID:7163635 Merker PC et al; Res Commun Chem Pathol Pharmacol 38 (3): 367-88 (1982)

5.4 Metabolism/Metabolites

Specific data regarding the metabolism of resorcinol is not readily available, although the major metabolite of resorcinol found in the urine was its glucuronide.

It yields 3-amino-3,4-dihydro-7-hydroxycoumarin, 2,4-di- hydroxy-l-phenylalanine, m-hydroxy-beta-d-fucoside, & m-hydroxy- phenyl-beta-d-glucoside in Escherichia /from table/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. R-1

It yields m-hydroxyphenyl-alpha-d-glucoside & hydroxyquinol in Aspergillus; yields m-hydroxyphenyl sulfate & m-hydroxyphenyl-beta-d-glucuronide in rabbits. /From table/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. R-1

Resorcinol yields m-methoxyphenol in streptomyces. /From table/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. R-2

In the urine, the major metabolite of resorcinol was its glucuronide.

PMID:7163635 Merker PC et al; Res Commun Chem Pathol Pharmacol 38 (3): 367-88 (1982)

For more Metabolism/Metabolites (Complete) data for RESORCINOL (6 total), please visit the HSDB record page.

5.5 Biological Half-Life

Specific data regarding the half-life of resorcinol is not readily available, although, in one case of dermal exposure, an adult male with a 90% phenol exposure had an elimination half-life of about 14 hours.

5.6 Mechanism of Action

Data regarding the specific mechanisms of action of resorcinol does not appear to be readily accessible in the literature. Nevertheless, the effectiveness of the agent in treating various topical, dermatological conditions by eliciting antibacterial and keratolytic actions appears to stem from resorcinol's propensity for protein precipitation. In particular, it appears that resorcinol indicated for treating acne, dermatitis, or eczema in various skin care topical applications and peels revolves around the compound's ability to precipitate cutaneous proteins from the treated skin.

In animal studies resorcinol failed to induce thyroid gland (TG) toxicity, unless pharmacokinetic/toxicokinetic (PK/TK) conditions were manipulated (e.g., injection of resorcinol in oil or application in a slow release formulation). A recently completed two-generation reproductive toxicity study in rats did not detect any adverse effects on either reproductive or TG end points. Resorcinol intake via drinking water up to the palatability limit had resulted in average daily intakes (mg/kg) of 233 in F0 and F1 males and 304 (premating/gestation) or 660 (lactation) in females. Free resorcinol in blood plasma was barely detectable in a few parental animals, indicating rapid metabolism. This short review communication offers a perspective on compromised human skin barrier function as a likely cause of drastic increases in resorcinol absorption. In conjunction with multiple daily applications over many months to hyperemic, inflamed, and lesioned human skin much higher absorption was likely responsible for the reported human TG toxicity.

PMID:18293213 Welsch F. Int J Toxicol. 27(1):59-63. (2008).

Phenols oxidizable to quinones cause cessation of protoplasmic streaming in nitella & elodea canadensis, also inhibiting adenosine triphosphatase activity. /Phenols/

STOM DI, ROGOZINA NA; EKSP VODN TOKSIKOL 6: 111-118 (1976)

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LIMITED","customerCountry":"INDIA","quantity":"14000.00","actualQuantity":"14000","unit":"KGS","unitRateFc":"5","totalValueFC":"70808.2","currency":"USD","unitRateINR":"420","date":"31-Aug-2024","totalValueINR":"5880105","totalValueInUsd":"70808.2","indian_port":"Hyderabad ICD","hs_no":"29072100","bill_no":"5346147","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI","supplierAddress":"4TH FLOOR,IWAMOTOCHO TOYO BLDG1-2 IWAMOTOCHO3-CHOME CHIYODA-KU TOKYO 101-0032 JP","customerAddress":"SY NO 296\/7\/9, IDA"}]

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Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country	Total Quantity (KGS)	Average Price (USD/KGS)	Number of Transactions

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List of Related Excipient Companies and Suppliers of Tox21_300140 by Shanghai Shenmei Pharmaceutical Technology Co Ltd on PharmaCompass.com

Tox21_300140

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CHEMISTRY

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ACTIVE PHARMA INGREDIENTS

2 API Suppliers

2 Listed Suppliers

$ API Reference Price

FINISHED DOSAGE FORMULATIONS

2 FDF Dossiers

1 Europe

1 South Africa

RELATED EXCIPIENT COMPANIES

1 Evonik

3 Rochem International Inc

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6 DKSH

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5 Aeon Procare

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20 BASF

1 Clariant

5 Corel Pharma Chem

2 Finar

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2 Ingredion Pharma Solutions

10 Kerry

5 Lubrizol Life Science Health

2 Microlex e.U

4 Pluviaendo

15 Roquette

4 Seppic

1 Shandong Focus Biotechnology Co., Ltd

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1 Sigachi Industries

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EXCIPIENTS BY APPLICATIONS

40 Topical

22 Fillers, Diluents & Binders

21 Coating Systems & Additives

17 Direct Compression

17 Thickeners and Stabilizers

14 Solubilizers

13 Co-Processed Excipients

12 Controlled & Modified Release

12 Parenteral

10 Taste Masking

10 Film Formers & Plasticizers

9 Granulation

9 Lubricants & Glidants

6 Surfactant & Foaming Agents

6 Rheology Modifiers

4 Emulsifying Agents

4 Chewable & Orodispersible Aids

4 Disintegrants & Superdisintegrants

2 Coloring Agents

2 API Stability Enhancers

GLOBAL SALES INFORMATION

1 Finished Drug Prices

MARKET PLACE

6 APIs

REF. STANDARDS & IMPURITIES

1 Others

ACTIVE PHARMA INGREDIENTS

API REF. PRICE (USD/KG)

$ 12

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PATENTS & EXCLUSIVITIES

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