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1. Resorcin
2. Resorcinol Disodium Salt
3. Resorcinol, Monocopper (2+) Salt
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)
| Molecular Weight | 110.11 g/mol |
|---|---|
| Molecular Formula | C6H6O2 |
| 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 Ų |
| 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 |
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
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.
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.
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
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)
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.
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.
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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