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Agatolimod

Agatolimod (also known as CpG 7909, ODN 2006, PF-3512676, VaxImmune, and ProMuneT) is a CpG Oligodeoxynucleotide which acts as a toll-like receptor 9 agonist. Agatolimod stimulates the immune system and has been tested for prevention and treatment of cancer, infectious diseases, allergies, and asthma. [1]

Agatolimod
Identifiers
  • 207623-20-9 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 48284824
  • 56841789
UNII
  • 5V336PV3HG Y
  • InChI=1S/C236H303N70O133P23S23/c1-91-47-287(223(333)269-193(91)309)157-23-105(308)130(394-157)62-370-440(347,463)422-111-29-163(289-49-93(3)195(311)271-225(289)335)399-135(111)67-381-457(364,480)434-123-41-175(301-85-247-181-187(301)257-213(241)263-207(181)323)412-148(123)80-388-443(350,466)419-108-26-159(284-20-16-154(238)254-220(284)330)396-132(108)64-373-447(354,470)424-113-31-165(291-51-95(5)197(313)273-227(291)337)407-143(113)75-383-461(368,484)438-127-45-179(305-89-251-185-191(305)261-217(245)267-211(185)327)415-151(127)83-391-455(362,478)432-121-39-173(299-59-103(13)205(321)281-235(299)345)404-140(121)72-379-451(358,474)428-117-35-169(295-55-99(9)201(317)277-231(295)341)400-136(117)68-376-450(357,473)427-116-34-168(294-54-98(8)200(316)276-230(294)340)403-139(116)71-378-454(361,477)431-120-38-172(298-58-102(12)204(320)280-234(298)344)410-146(120)78-386-460(367,483)437-126-44-178(304-88-250-184-190(304)260-216(244)266-210(184)326)414-150(126)82-390-445(352,468)421-110-28-161(286-22-18-156(240)256-222(286)332)398-134(110)66-374-448(355,471)425-114-32-166(292-52-96(6)198(314)274-228(292)338)408-144(114)76-384-462(369,485)439-128-46-180(306-90-252-186-192(306)262-218(246)268-212(186)328)416-152(128)84-392-456(363,479)433-122-40-174(300-60-104(14)206(322)282-236(300)346)405-141(122)73-380-452(359,475)429-118-36-170(296-56-100(10)202(318)278-232(296)342)401-137(118)69-375-449(356,472)426-115-33-167(293-53-97(7)199(315)275-229(293)339)402-138(115)70-377-453(360,476)430-119-37-171(297-57-101(11)203(319)279-233(297)343)409-145(119)77-385-459(366,482)436-125-43-177(303-87-249-183-189(303)259-215(243)265-209(183)325)413-149(125)81-389-444(351,467)420-109-27-160(285-21-17-155(239)255-221(285)331)397-133(109)65-372-446(353,469)423-112-30-164(290-50-94(4)196(312)272-226(290)336)406-142(112)74-382-458(365,481)435-124-42-176(302-86-248-182-188(302)258-214(242)264-208(182)324)411-147(124)79-387-442(349,465)418-107-25-158(283-19-15-153(237)253-219(283)329)395-131(107)63-371-441(348,464)417-106-24-162(393-129(106)61-307)288-48-92(2)194(310)270-224(288)334/h15-22,47-60,85-90,105-152,157-180,307-308H,23-46,61-84H2,1-14H3,(H,347,463)(H,348,464)(H,349,465)(H,350,466)(H,351,467)(H,352,468)(H,353,469)(H,354,470)(H,355,471)(H,356,472)(H,357,473)(H,358,474)(H,359,475)(H,360,476)(H,361,477)(H,362,478)(H,363,479)(H,364,480)(H,365,481)(H,366,482)(H,367,483)(H,368,484)(H,369,485)(H2,237,253,329)(H2,238,254,330)(H2,239,255,331)(H2,240,256,332)(H,269,309,333)(H,270,310,334)(H,271,311,335)(H,272,312,336)(H,273,313,337)(H,274,314,338)(H,275,315,339)(H,276,316,340)(H,277,317,341)(H,278,318,342)(H,279,319,343)(H,280,320,344)(H,281,321,345)(H,282,322,346)(H3,241,257,263,323)(H3,242,258,264,324)(H3,243,259,265,325)(H3,244,260,266,326)(H3,245,261,267,327)(H3,246,262,268,328)/t105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129+,130+,131+,132+,133+,134+,135+,136+,137+,138+,139+,140+,141+,142+,143+,144+,145+,146+,147+,148+,149+,150+,151+,152+,157+,158+,159+,160+,161+,162+,163+,164+,165+,166+,167+,168+,169+,170+,171+,172+,173+,174+,175+,176+,177+,178+,179+,180+,440?,441?,442?,443?,444?,445?,446?,447?,448?,449?,450?,451?,452?,453?,454?,455?,456?,457?,458?,459?,460?,461?,462?/m0/s1
    Key: KQQWAOVVQRSHRC-CPSXWDTOSA-N
  • InChI=1/C236H303N70O133P23S23/c1-91-47-287(223(333)269-193(91)309)157-23-105(308)130(394-157)62-370-440(347,463)422-111-29-163(289-49-93(3)195(311)271-225(289)335)399-135(111)67-381-457(364,480)434-123-41-175(301-85-247-181-187(301)257-213(241)263-207(181)323)412-148(123)80-388-443(350,466)419-108-26-159(284-20-16-154(238)254-220(284)330)396-132(108)64-373-447(354,470)424-113-31-165(291-51-95(5)197(313)273-227(291)337)407-143(113)75-383-461(368,484)438-127-45-179(305-89-251-185-191(305)261-217(245)267-211(185)327)415-151(127)83-391-455(362,478)432-121-39-173(299-59-103(13)205(321)281-235(299)345)404-140(121)72-379-451(358,474)428-117-35-169(295-55-99(9)201(317)277-231(295)341)400-136(117)68-376-450(357,473)427-116-34-168(294-54-98(8)200(316)276-230(294)340)403-139(116)71-378-454(361,477)431-120-38-172(298-58-102(12)204(320)280-234(298)344)410-146(120)78-386-460(367,483)437-126-44-178(304-88-250-184-190(304)260-216(244)266-210(184)326)414-150(126)82-390-445(352,468)421-110-28-161(286-22-18-156(240)256-222(286)332)398-134(110)66-374-448(355,471)425-114-32-166(292-52-96(6)198(314)274-228(292)338)408-144(114)76-384-462(369,485)439-128-46-180(306-90-252-186-192(306)262-218(246)268-212(186)328)416-152(128)84-392-456(363,479)433-122-40-174(300-60-104(14)206(322)282-236(300)346)405-141(122)73-380-452(359,475)429-118-36-170(296-56-100(10)202(318)278-232(296)342)401-137(118)69-375-449(356,472)426-115-33-167(293-53-97(7)199(315)275-229(293)339)402-138(115)70-377-453(360,476)430-119-37-171(297-57-101(11)203(319)279-233(297)343)409-145(119)77-385-459(366,482)436-125-43-177(303-87-249-183-189(303)259-215(243)265-209(183)325)413-149(125)81-389-444(351,467)420-109-27-160(285-21-17-155(239)255-221(285)331)397-133(109)65-372-446(353,469)423-112-30-164(290-50-94(4)196(312)272-226(290)336)406-142(112)74-382-458(365,481)435-124-42-176(302-86-248-182-188(302)258-214(242)264-208(182)324)411-147(124)79-387-442(349,465)418-107-25-158(283-19-15-153(237)253-219(283)329)395-131(107)63-371-441(348,464)417-106-24-162(393-129(106)61-307)288-48-92(2)194(310)270-224(288)334/h15-22,47-60,85-90,105-152,157-180,307-308H,23-46,61-84H2,1-14H3,(H,347,463)(H,348,464)(H,349,465)(H,350,466)(H,351,467)(H,352,468)(H,353,469)(H,354,470)(H,355,471)(H,356,472)(H,357,473)(H,358,474)(H,359,475)(H,360,476)(H,361,477)(H,362,478)(H,363,479)(H,364,480)(H,365,481)(H,366,482)(H,367,483)(H,368,484)(H,369,485)(H2,237,253,329)(H2,238,254,330)(H2,239,255,331)(H2,240,256,332)(H,269,309,333)(H,270,310,334)(H,271,311,335)(H,272,312,336)(H,273,313,337)(H,274,314,338)(H,275,315,339)(H,276,316,340)(H,277,317,341)(H,278,318,342)(H,279,319,343)(H,280,320,344)(H,281,321,345)(H,282,322,346)(H3,241,257,263,323)(H3,242,258,264,324)(H3,243,259,265,325)(H3,244,260,266,326)(H3,245,261,267,327)(H3,246,262,268,328)/t105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129+,130+,131+,132+,133+,134+,135+,136+,137+,138+,139+,140+,141+,142+,143+,144+,145+,146+,147+,148+,149+,150+,151+,152+,157+,158+,159+,160+,161+,162+,163+,164+,165+,166+,167+,168+,169+,170+,171+,172+,173+,174+,175+,176+,177+,178+,179+,180+,440?,441?,442?,443?,444?,445?,446?,447?,448?,449?,450?,451?,452?,453?,454?,455?,456?,457?,458?,459?,460?,461?,462?/m0/s1
    Key: KQQWAOVVQRSHRC-CPSXWDTOBP
  • Cc1cn(c(=O)[nH]c1=O)[C@H]2C[C@@H]([C@H](O2)COP(=S)(O)O[C@H]3C[C@@H](O[C@@H]3COP(=S)(O)O[C@H]4C[C@@H](O[C@@H]4COP(=S)(O)O[C@H]5C[C@@H](O[C@@H]5COP(=S)(O)O[C@H]6C[C@@H](O[C@@H]6COP(=S)(O)O[C@H]7C[C@@H](O[C@@H]7COP(=S)(O)O[C@H]8C[C@@H](O[C@@H]8COP(=S)(O)O[C@H]9C[C@@H](O[C@@H]9COP(=S)(O)O[C@H]1C[C@@H](O[C@@H]1COP(=S)(O)O[C@H]1C[C@@H](O[C@@H]1COP(=S)(O)O[C@H]1C[C@@H](O[C@@H]1COP(=S)(O)O[C@H]1C[C@@H](O[C@@H]1COP(=S)(O)O[C@H]1C[C@@H](O[C@@H]1COP(=S)(O)O[C@H]1C[C@@H](O[C@@H]1COP(=S)(O)O[C@H]1C[C@@H](O[C@@H]1COP(=S)(O)O[C@H]1C[C@@H](O[C@@H]1COP(=S)(O)O[C@H]1C[C@@H](O[C@@H]1COP(=S)(O)O[C@H]1C[C@@H](O[C@@H]1COP(=S)(O)O[C@H]1C[C@@H](O[C@@H]1COP(=S)(O)O[C@H]1C[C@@H](O[C@@H]1COP(=S)(O)O[C@H]1C[C@@H](O[C@@H]1COP(=S)(O)O[C@H]1C[C@@H](O[C@@H]1COP(=S)(O)O[C@H]1C[C@@H](O[C@@H]1COP(=S)(O)O[C@H]1C[C@@H](O[C@@H]1CO)n1cc(c(=O)[nH]c1=O)C)n1ccc(nc1=O)N)n1cnc2c1nc([nH]c2=O)N)n1cc(c(=O)[nH]c1=O)C)n1ccc(nc1=O)N)n1cnc2c1nc([nH]c2=O)N)n1cc(c(=O)[nH]c1=O)C)n1cc(c(=O)[nH]c1=O)C)n1cc(c(=O)[nH]c1=O)C)n1cc(c(=O)[nH]c1=O)C)n1cnc2c1nc([nH]c2=O)N)n1cc(c(=O)[nH]c1=O)C)n1ccc(nc1=O)N)n1cnc2c1nc([nH]c2=O)N)n1cc(c(=O)[nH]c1=O)C)n1cc(c(=O)[nH]c1=O)C)n1cc(c(=O)[nH]c1=O)C)n1cc(c(=O)[nH]c1=O)C)n1cnc2c1nc([nH]c2=O)N)n1cc(c(=O)[nH]c1=O)C)n1ccc(nc1=O)N)n1cnc2c1nc([nH]c2=O)N)n1cc(c(=O)[nH]c1=O)C)O
Properties
C236H303N70O133P23S23
Molar mass 7698.212
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Sequence edit

Agatolimod is composed of 24 deoxyribonucleotides in the following sequence:

(T-C-G-T-C-G-T-T-T-T-G-T-C-G-T-T-T-T-G-T-C-G-T-T)

References edit

  1. ^ "CpG 7909: PF 3512676, PF-3512676". Drugs in R&D. 7 (5): 312–316. 2006. doi:10.2165/00126839-200607050-00004. PMID 16922592. S2CID 195344824.

agatolimod, also, known, 7909, 2006, 3512676, vaximmune, promunet, oligodeoxynucleotide, which, acts, toll, like, receptor, agonist, stimulates, immune, system, been, tested, prevention, treatment, cancer, infectious, diseases, allergies, asthma, identifiers, . Agatolimod also known as CpG 7909 ODN 2006 PF 3512676 VaxImmune and ProMuneT is a CpG Oligodeoxynucleotide which acts as a toll like receptor 9 agonist Agatolimod stimulates the immune system and has been tested for prevention and treatment of cancer infectious diseases allergies and asthma 1 Agatolimod Identifiers CAS Number 207623 20 9 Y 3D model JSmol Interactive image ChemSpider 48284824 PubChem CID 56841789 UNII 5V336PV3HG Y InChI InChI 1S C236H303N70O133P23S23 c1 91 47 287 223 333 269 193 91 309 157 23 105 308 130 394 157 62 370 440 347 463 422 111 29 163 289 49 93 3 195 311 271 225 289 335 399 135 111 67 381 457 364 480 434 123 41 175 301 85 247 181 187 301 257 213 241 263 207 181 323 412 148 123 80 388 443 350 466 419 108 26 159 284 20 16 154 238 254 220 284 330 396 132 108 64 373 447 354 470 424 113 31 165 291 51 95 5 197 313 273 227 291 337 407 143 113 75 383 461 368 484 438 127 45 179 305 89 251 185 191 305 261 217 245 267 211 185 327 415 151 127 83 391 455 362 478 432 121 39 173 299 59 103 13 205 321 281 235 299 345 404 140 121 72 379 451 358 474 428 117 35 169 295 55 99 9 201 317 277 231 295 341 400 136 117 68 376 450 357 473 427 116 34 168 294 54 98 8 200 316 276 230 294 340 403 139 116 71 378 454 361 477 431 120 38 172 298 58 102 12 204 320 280 234 298 344 410 146 120 78 386 460 367 483 437 126 44 178 304 88 250 184 190 304 260 216 244 266 210 184 326 414 150 126 82 390 445 352 468 421 110 28 161 286 22 18 156 240 256 222 286 332 398 134 110 66 374 448 355 471 425 114 32 166 292 52 96 6 198 314 274 228 292 338 408 144 114 76 384 462 369 485 439 128 46 180 306 90 252 186 192 306 262 218 246 268 212 186 328 416 152 128 84 392 456 363 479 433 122 40 174 300 60 104 14 206 322 282 236 300 346 405 141 122 73 380 452 359 475 429 118 36 170 296 56 100 10 202 318 278 232 296 342 401 137 118 69 375 449 356 472 426 115 33 167 293 53 97 7 199 315 275 229 293 339 402 138 115 70 377 453 360 476 430 119 37 171 297 57 101 11 203 319 279 233 297 343 409 145 119 77 385 459 366 482 436 125 43 177 303 87 249 183 189 303 259 215 243 265 209 183 325 413 149 125 81 389 444 351 467 420 109 27 160 285 21 17 155 239 255 221 285 331 397 133 109 65 372 446 353 469 423 112 30 164 290 50 94 4 196 312 272 226 290 336 406 142 112 74 382 458 365 481 435 124 42 176 302 86 248 182 188 302 258 214 242 264 208 182 324 411 147 124 79 387 442 349 465 418 107 25 158 283 19 15 153 237 253 219 283 329 395 131 107 63 371 441 348 464 417 106 24 162 393 129 106 61 307 288 48 92 2 194 310 270 224 288 334 h15 22 47 60 85 90 105 152 157 180 307 308H 23 46 61 84H2 1 14H3 H 347 463 H 348 464 H 349 465 H 350 466 H 351 467 H 352 468 H 353 469 H 354 470 H 355 471 H 356 472 H 357 473 H 358 474 H 359 475 H 360 476 H 361 477 H 362 478 H 363 479 H 364 480 H 365 481 H 366 482 H 367 483 H 368 484 H 369 485 H2 237 253 329 H2 238 254 330 H2 239 255 331 H2 240 256 332 H 269 309 333 H 270 310 334 H 271 311 335 H 272 312 336 H 273 313 337 H 274 314 338 H 275 315 339 H 276 316 340 H 277 317 341 H 278 318 342 H 279 319 343 H 280 320 344 H 281 321 345 H 282 322 346 H3 241 257 263 323 H3 242 258 264 324 H3 243 259 265 325 H3 244 260 266 326 H3 245 261 267 327 H3 246 262 268 328 t105 106 107 108 109 110 111 112 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 157 158 159 160 161 162 163 164 165 166 167 168 169 170 171 172 173 174 175 176 177 178 179 180 440 441 442 443 444 445 446 447 448 449 450 451 452 453 454 455 456 457 458 459 460 461 462 m0 s1Key KQQWAOVVQRSHRC CPSXWDTOSA NInChI 1 C236H303N70O133P23S23 c1 91 47 287 223 333 269 193 91 309 157 23 105 308 130 394 157 62 370 440 347 463 422 111 29 163 289 49 93 3 195 311 271 225 289 335 399 135 111 67 381 457 364 480 434 123 41 175 301 85 247 181 187 301 257 213 241 263 207 181 323 412 148 123 80 388 443 350 466 419 108 26 159 284 20 16 154 238 254 220 284 330 396 132 108 64 373 447 354 470 424 113 31 165 291 51 95 5 197 313 273 227 291 337 407 143 113 75 383 461 368 484 438 127 45 179 305 89 251 185 191 305 261 217 245 267 211 185 327 415 151 127 83 391 455 362 478 432 121 39 173 299 59 103 13 205 321 281 235 299 345 404 140 121 72 379 451 358 474 428 117 35 169 295 55 99 9 201 317 277 231 295 341 400 136 117 68 376 450 357 473 427 116 34 168 294 54 98 8 200 316 276 230 294 340 403 139 116 71 378 454 361 477 431 120 38 172 298 58 102 12 204 320 280 234 298 344 410 146 120 78 386 460 367 483 437 126 44 178 304 88 250 184 190 304 260 216 244 266 210 184 326 414 150 126 82 390 445 352 468 421 110 28 161 286 22 18 156 240 256 222 286 332 398 134 110 66 374 448 355 471 425 114 32 166 292 52 96 6 198 314 274 228 292 338 408 144 114 76 384 462 369 485 439 128 46 180 306 90 252 186 192 306 262 218 246 268 212 186 328 416 152 128 84 392 456 363 479 433 122 40 174 300 60 104 14 206 322 282 236 300 346 405 141 122 73 380 452 359 475 429 118 36 170 296 56 100 10 202 318 278 232 296 342 401 137 118 69 375 449 356 472 426 115 33 167 293 53 97 7 199 315 275 229 293 339 402 138 115 70 377 453 360 476 430 119 37 171 297 57 101 11 203 319 279 233 297 343 409 145 119 77 385 459 366 482 436 125 43 177 303 87 249 183 189 303 259 215 243 265 209 183 325 413 149 125 81 389 444 351 467 420 109 27 160 285 21 17 155 239 255 221 285 331 397 133 109 65 372 446 353 469 423 112 30 164 290 50 94 4 196 312 272 226 290 336 406 142 112 74 382 458 365 481 435 124 42 176 302 86 248 182 188 302 258 214 242 264 208 182 324 411 147 124 79 387 442 349 465 418 107 25 158 283 19 15 153 237 253 219 283 329 395 131 107 63 371 441 348 464 417 106 24 162 393 129 106 61 307 288 48 92 2 194 310 270 224 288 334 h15 22 47 60 85 90 105 152 157 180 307 308H 23 46 61 84H2 1 14H3 H 347 463 H 348 464 H 349 465 H 350 466 H 351 467 H 352 468 H 353 469 H 354 470 H 355 471 H 356 472 H 357 473 H 358 474 H 359 475 H 360 476 H 361 477 H 362 478 H 363 479 H 364 480 H 365 481 H 366 482 H 367 483 H 368 484 H 369 485 H2 237 253 329 H2 238 254 330 H2 239 255 331 H2 240 256 332 H 269 309 333 H 270 310 334 H 271 311 335 H 272 312 336 H 273 313 337 H 274 314 338 H 275 315 339 H 276 316 340 H 277 317 341 H 278 318 342 H 279 319 343 H 280 320 344 H 281 321 345 H 282 322 346 H3 241 257 263 323 H3 242 258 264 324 H3 243 259 265 325 H3 244 260 266 326 H3 245 261 267 327 H3 246 262 268 328 t105 106 107 108 109 110 111 112 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 157 158 159 160 161 162 163 164 165 166 167 168 169 170 171 172 173 174 175 176 177 178 179 180 440 441 442 443 444 445 446 447 448 449 450 451 452 453 454 455 456 457 458 459 460 461 462 m0 s1Key KQQWAOVVQRSHRC CPSXWDTOBP SMILES Cc1cn c O nH c1 O C H 2C C H C H O2 COP S O O C H 3C C H O C H 3COP S O O C H 4C C H O C H 4COP S O O C H 5C C H O C H 5COP S O O C H 6C C H O C H 6COP S O O C H 7C C H O C H 7COP S O O C H 8C C H O C H 8COP S O O C H 9C C H O C H 9COP S O O C H 1C C H O C H 1COP S O O C H 1C C H O C H 1COP S O O C H 1C C H O C H 1COP S O O C H 1C C H O C H 1COP S O O C H 1C C H O C H 1COP S O O C H 1C C H O C H 1COP S O O C H 1C C H O C H 1COP S O O C H 1C C H O C H 1COP S O O C H 1C C H O C H 1COP S O O C H 1C C H O C H 1COP S O O C H 1C C H O C H 1COP S O O C H 1C C H O C H 1COP S O O C H 1C C H O C H 1COP S O O C H 1C C H O C H 1COP S O O C H 1C C H O C H 1COP S O O C H 1C C H O C H 1CO n1cc c O nH c1 O C n1ccc nc1 O N n1cnc2c1nc nH c2 O N n1cc c O nH c1 O C n1ccc nc1 O N n1cnc2c1nc nH c2 O N n1cc c O nH c1 O C n1cc c O nH c1 O C n1cc c O nH c1 O C n1cc c O nH c1 O C n1cnc2c1nc nH c2 O N n1cc c O nH c1 O C n1ccc nc1 O N n1cnc2c1nc nH c2 O N n1cc c O nH c1 O C n1cc c O nH c1 O C n1cc c O nH c1 O C n1cc c O nH c1 O C n1cnc2c1nc nH c2 O N n1cc c O nH c1 O C n1ccc nc1 O N n1cnc2c1nc nH c2 O N n1cc c O nH c1 O C O Properties Chemical formula C236H303N70O133P23S23 Molar mass 7698 212 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesSequence editAgatolimod is composed of 24 deoxyribonucleotides in the following sequence T C G T C G T T T T G T C G T T T T G T C G T T References edit CpG 7909 PF 3512676 PF 3512676 Drugs in R amp D 7 5 312 316 2006 doi 10 2165 00126839 200607050 00004 PMID 16922592 S2CID 195344824 Retrieved from https en wikipedia org w index php title Agatolimod amp oldid 979755275, wikipedia, wiki, book, books, library,

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